It seems to me that makes sense. I ran some calculations, in my Chem3D, and I found out I can do dihedral conformation calculations. I've attached the results below:
If you can't tell we are looking at it from the "front" with the two groups pointing towards us. The acid obviously in the equatorial position of the "chair" conformation. Pink dots are electron pairs. Although, I'm not sure why it doesn't include the pair on the carbonyl or the nitrogen...
You can see that there are two local energy minima (one at 25.15 and 29.10 kcal/mol).
The first image, #1, is the higher of the two states, the 2nd image, is the lower energy conformation. You can see that in the lower image, the carbonyl is facing the other lone pairs of the methyl ester and that in the higher conformation, the lone pairs of the carbamate are now pointing towards the ester, but still can interact with the acid carbonyl.
The highest conformation, I've also attached for reference. Hope this is helpful in solving your problem!
EDIT: Wow, images too big, back up in a sec.
Ok, hmm..images are very blurry it seems, hopefully it illustrates the point though. Also, is there an easy way to remove the colored backgrounds? That's what happens when I drop it in paint.