(S)-cyclopentyl 2-amino-4-methylpentanoate → HCID 57658455, compound

HRID 1667372Notes

Reaction equation

HRID 1667372 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:22]=[CH:21][C:11]([O:12][CH2:13][CH2:14][CH2:15]OS(C)(=O)=O)=[CH:10][CH:9]=2)[C:6](=[O:23])[CH:5]=[CH:4][C:3]=1[C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH3:32])[CH:26]=1.[CH:34]1([O:39][C:40](=[O:47])[C@H:41]([CH2:43][CH:44]([CH3:46])[CH3:45])[NH2:42])[CH2:38][CH2:37][CH2:36][CH2:35]1>>[NH2:1][C:2]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][CH2:15][NH:42][C@@H:41]([CH2:43][CH:44]([CH3:46])[CH3:45])[C:40]([O:39][CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[O:47])=[CH:21][CH:22]=2)[C:6](=[O:23])[CH:5]=[CH:4][C:3]=1[C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH3:32])[CH:26]=1

Participants

3

Reactant 2

HCID 53718217(S)-cyclopentyl 2-amino-4-methylpentanoate2×HCID 57658379HCID 57658379, compound

Product 1

HCID 57658455HCID 57658455, compound

Procedure

From Intermediate 4A and L-leucine cyclopentyl ester (Intermediate 8), LCMS purity 89%, m/z 578 [M+H]+, 1H NMR (400 MHz, d6-DMSO), δ: 0.95 (6H, m), 1.55-2.25 (12H, m), 2.30 (3H, m), 2.75-3.30 (2H, m), 4.15 (3H, m), 5.25 (1H, m), 5.70 (1H, d). 7.15 (2H, d), 7.30-7.40 (4H, m), 7.40-7.50 (2H, m).

Sources & evidence

ORD record
ord-a7ad79711bbb43c7aac7c488ffb38b1c
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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