L-Serine → (2S)-N-[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-3-hydroxy-2-[(2-naphthalenylsulfonyl)amino]propanamide hydrochloride

HRID 636914Notes

Reaction equation

HRID 636914 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][CH:14]([NH:23][C:24](=[O:45])[CH2:25][NH:26][S:27]([C:30]3[C:31]([CH3:44])=[C:32]([CH3:43])[C:33]4OC(C)(C)[CH2:36][CH2:35][C:34]=4[C:41]=3C)(=[O:29])=[O:28])[C:15](=[O:22])[N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[OH:46][CH2:47][C@H](NS(C1C=CC2C(=CC=CC=2)C=1)(=O)=O)C(O)=O.N[C@H](C(O)=O)CO.C1C2C(=CC=CC=2)C=CC=1S([Cl:86])(=O)=O>>[ClH:86].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][CH:14]([NH:23][C:24](=[O:45])[C@@H:25]([NH:26][S:27]([C:30]3[CH:31]=[CH:44][C:33]4[C:34](=[CH:35][CH:36]=[CH:43][CH:32]=4)[CH:41]=3)(=[O:29])=[O:28])[CH2:47][OH:46])[C:15](=[O:22])[N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 4

HCID 5951L-SerineHCID 71252-Naphthalenesulfonyl chlorideHCID 14030411(2S)-3-hydroxy-2-[(2-naphthalenylsulfonyl)amino]propanoic acidHCID 22665631N-[1-[(1-Amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[[(3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-yl)sulfonyl]amino]acetamide hydrochloride

Product 1

HCID 69781330(2S)-N-[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-3-hydroxy-2-[(2-naphthalenylsulfonyl)amino]propanamide hydrochloride

Procedure

The procedure described for 5c was used. Deprotection of Sa and coupling with (2S)-3-hydroxy-2-[(2-naphthalenylsulfonyl)amino]propanoic acid (prepared from L-serine and 2-naphthalenylsulfonylchloride using the procedure described for 5b) yielded 7. 1H-NMR 200 MHz (CD3OD) δ: 1.12-1.58 (6H, m), 2.57-2.69 (1H, m) 2.95-3.95 (8H, m), 4.9-5.1 (1H, m), 7.11-7.22 (1H, m), 7.43-8.16 (9H, m), 8.24-8.34 (1H, m), 8.41-8.45 (1H, m).

Workup

  1. customyielded 7

Sources & evidence

ORD record
ord-5f2f7f1899454580946af47665cf1726
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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