4-((Benzyloxy)carbonyl)-1-((tert-butoxy)carbonyl)piperazine-2-carboxylic acid → (1-tert-Butoxycarbonyl-4-Benzyloxycarbonylpiperazin-2-ylcarbonyl)-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide

HRID 2185439Notes

Reaction equation

HRID 2185439 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:31])[C@@H:13]2[CH2:17][C@@H:16]([NH:18][C:19](=[O:30])[C@H:20]([OH:29])[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:15][NH:14]2)[CH:2]=1.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[O:46])[CH2:41][CH:40]1[C:55](O)=[O:56])=[O:38])([CH3:35])([CH3:34])[CH3:33].N1C2C(=CC=CC=2)C=C(NC(=O)[C@@H]2C[C@@H](NC(=O)[C@H](O)CCC3C=CC=CC=3)CN2C(=O)[C@@H]2C[C@@H](NC(OC(C)(C)C)=O)CN2C(OC(C)(C)C)=O)C=1>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:31])[C@@H:13]2[CH2:17][C@@H:16]([NH:18][C:19](=[O:30])[C@H:20]([OH:29])[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:15][N:14]2[C:55]([CH:40]2[CH2:41][N:42]([C:45]([O:47][CH2:48][C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)=[O:46])[CH2:43][CH2:44][N:39]2[C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:38])=[O:56])[CH:2]=1

Participants

4

Reactant 3

HCID 27567784-((Benzyloxy)carbonyl)-1-((tert-butoxy)carbonyl)piperazine-2-carboxylic acidHCID 21341547N-tert-Butoxycarbonyl-trans-4-(N-tert-Butoxycarbonylamino)-L-Prolyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-QuinolylamideHCID 59895122trans-4-((R)-2-Hydroxy-4-Phenylbutrylamino)-L-Proline 3-Quinolylamide

Product 1

HCID 21341445(1-tert-Butoxycarbonyl-4-Benzyloxycarbonylpiperazin-2-ylcarbonyl)-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide

Procedure

trans-4-((R)-2-hydroxy-4-phenybutyrylamino)-L-proline 3-quinolylamide (Compound D101 (H), 272 mg) and 1-tert-butoxycarbonyl-4-benzyloxycarbonylpiperazine-2-ylcarboxylic acid (A, 237 mg) were coupled using the same procedure of Compound D101 (P) to afford the title compound (171 mg) as a colorless glassy solid: mass spectrum (FAB+) m/e 765 (M+1).

Sources & evidence

ORD record
ord-d631619bafde40f09ef877ec7673ff3f
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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