tert-Butyl piperazine-1-carboxylate → HCID 86620601, compound

HRID 1685547Notes

Reaction equation

HRID 1685547 reaction equation
[CH:1]1([CH2:6][C@H:7]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[C:8]([NH:10][C:11]2[S:12][C:13]([S:16][CH2:17][C:18](O)=[O:19])=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]>>[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][N:41]([C:18](=[O:19])[CH2:17][S:16][C:13]2[S:12][C:11]([NH:10][C:8](=[O:9])[C@@H:7]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:28])=[O:29])=[CH:23][CH:22]=3)[CH2:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[N:15][CH:14]=2)[CH2:40][CH2:39]1)=[O:37])([CH3:34])([CH3:32])[CH3:33]

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 11597971HCID 11597971, compound

Product 1

HCID 86620601HCID 86620601, compound

Procedure

(R)-4-(2-{2-[3-Cyclopentyl-2-(4-methanesulfonyl-phenyl)propionylamino]-thiazol-5-ylsulfanyl}-acetyl)-piperazine-1-carboxylic acid tert-butyl ester was prepared from (R)-{2-[3-cyclopentyl-2-(4-methanesulfonyl-phenyl)propionylamino]-thiazol-5-ylsulfanyl}-acetic acid and tert-butyl-1-piperazinecarboxylate as described in Example 12. 1H-NMR (CDCl3): δ 7.87 (d, 2H), 7.54 (d, 2H), 7.44 (s, 1H), 3.87 (t, 1H), 3.66 (s, 2H), 3.61-3.46 (m, 8H), 3.05 (s, 3H), 2.24 (m, 1H), 1.89 (m, 1H), 1.79-1.54 (m, 5H), 1.48 (m, 11H), 1.14 (m, 2H); HPLC-MS: m/z: 637 (M+1), 582 (M+1-C(CH3)3)

Sources & evidence

ORD record
ord-1f43278ebe73460b9bc04996e1610ca9
Source dataset
uspto-grants-2012_04
Patent number
US08148412B2

Reaction notes

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