N-(tert-Butoxycarbonyl)-L-cyclohexylglycine → cyclopentyl (2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)acetate

HRID 548213Notes

Reaction equation

HRID 548213 reaction equation
[CH:1]1(OC(=O)[C@@H](NC(OCC2C=CC=CC=2)=O)COC(C)(C)C)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:27]([O:31][C:32]([NH:34][C@@H:35]([CH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1)[C:36]([OH:38])=[O:37])=[O:33])([CH3:30])([CH3:29])[CH3:28]>>[CH:1]1([O:37][C:36](=[O:38])[C@@H:35]([NH:34][C:32]([O:31][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:33])[CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 7004938N-(tert-Butoxycarbonyl)-L-cyclohexylglycineHCID 57971607HCID 57971607, compound

Product 1

HCID 57658394cyclopentyl (2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)acetate

Procedure

This was prepared in the same manner as (S)-2-benzyloxycarbonylamino-3-tert-butoxy-propionic acid cyclopentyl ester (Method A, Stage 1) but from (S)-tert-butoxycarbonylamino-cyclohexyl acetic acid. 1H NMR (300 MHz, CDCl3), δ: 1.00-1.40 (10H, m, CH×10), 1.45 (9H, s, C(CH3)3), 1.60-2.00 (8H, m, 4×CH2), 4.15 (1H, m, CH), 5.05 (1H, d, NH, J=7.6 Hz), 5.25 (1H, m, CH).

Sources & evidence

ORD record
ord-cd4672b667fe459790f48f68502e25dd
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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