(S)-cyclopentyl 2-amino-4-methylpentanoate → HCID 57658393, compound

HRID 1667373Notes

Reaction equation

HRID 1667373 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([O:15][CH:16]3[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]3)=[CH:10][C:9]=2[F:23])[C:6](=[O:24])[CH:5]=[CH:4][C:3]=1[C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=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[C:13]([F:14])=[CH:12][C:11]([O:15][CH:16]3[CH2:21][CH2:20][CH:19]([NH:42][C@@H:41]([CH2:43][CH:44]([CH3:46])[CH3:45])[C:40]([O:39][CH:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[O:47])[CH2:18][CH2:17]3)=[CH:10][C:9]=2[F:23])[C:6](=[O:24])[CH:5]=[CH:4][C:3]=1[C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 53718217(S)-cyclopentyl 2-amino-4-methylpentanoate2×HCID 57658324HCID 57658324, compound

Product 1

HCID 57658393HCID 57658393, compound

Procedure

From Intermediate 5 (120 mg, 0.263 mmol) and L-Leucine cyclopentyl ester (Intermediate 8). LCMS purity 100%, m/z 640 [M+H]+, 1H NMR (400 MHz, CD3OD), δ: 0.95-1.05 (6H, m), 1.50-2.00 (16H, m), 2.10-2.35 (3H, m), 3.15-3.20 (1H, m), 4.00-4.15 (1H, m), 4.40 and 4.75 (0.5H each, m), 5.25-5.35 (1H, m), 5.75 (1H, d), 6.85-6.95 (2H, m), 7.15-7.25 (2H, m), 7.55-7.65 (2H, m), 7.65-7.70 (1H, m).

Sources & evidence

ORD record
ord-1dfd7a5c200d493384724946fe45fd2c
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

Loading…