Fmoc-D-cys(tbu)-OH → (S)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid cyclopentyl ester

HRID 548217Notes

Reaction equation

HRID 548217 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]([S:31][CH2:32][C@@H:33]([NH:37][C:38]([O:40][CH2:41][CH:42]1[C:54]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[C:48]2[C:43]1=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:39])[C:34]([OH:36])=[O:35])([CH3:30])([CH3:29])[CH3:28]>>[CH:1]1([O:35][C:34](=[O:36])[C@H:33]([NH:37][C:38]([O:40][CH2:41][CH:42]2[C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][C:48]=3[C:49]3[C:54]2=[CH:53][CH:52]=[CH:51][CH:50]=3)=[O:39])[CH2:32][S:31][C:27]([CH3:30])([CH3:28])[CH3:29])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 6992526Fmoc-D-cys(tbu)-OHHCID 57971607HCID 57971607, compound

Product 1

HCID 57971729(S)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid cyclopentyl ester

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)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid. 1H NMR (300 MHz, CDCl3), δ: 1.30 (9H, s, (CH3)3), 1.55-1.95 (8H, m, CH2×4), 3.05 (2H, d, CH2, J=4.8 Hz), 4.20-4.30 (1H, m, CH), 4.40 (2H, d, CH2, J=7.5 Hz), 4.65 (1H, m, CH), 5.25 (1H, m, CH), 5.70 (1H, d, NH, J=7.8 Hz), 7.30-7.50 (4H, m, ArH×4), 7.65 (2H, d, J=7.5 Hz, ArH×2), 7.80 (2H, d, J=7.5 Hz, ArH×2).

Sources & evidence

ORD record
ord-a4214d7a4ef34a7cb3213795efefd216
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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