Isoquinoline-1-carboxylic acid → Ethylmorpholine

HRID 1757730Notes

Reaction equation

HRID 1757730 reaction equation
C(O[C:6](=[O:32])[C@@H:7]1C[CH2:10][CH2:9][N:8]1[CH2:12][C@@H:13](O)[C@@H](NC(=O)[C@H](CC(=O)N)N)C[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C)(C)C.[C:33]1(C(O)=O)C2C(=CC=CC=2)C=C[N:34]=1.O[C:47]1[C:55]2[N:54]=NN[C:51]=2[CH:50]=[CH:49][CH:48]=1>>[CH2:9]([N:8]1[CH2:7][CH2:6][O:32][CH2:13][CH2:12]1)[CH3:10].[CH:55]1([N:54]=[C:33]=[N:34][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1

Participants

5

Reactant 3

HCID 68092Isoquinoline-1-carboxylic acidHCID 70041604N-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl esterHCID 178418300HCID 178418300, compound

Product 2

HCID 7525EthylmorpholineHCID 10868Dicyclohexylcarbodiimide

Procedure

In a manner analogous to that described in Example 27, from 234 mg of N-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester, 90 mg of 1-isoquinolinecarboxylic acid, 70 mg of hydroxybenzotriazole. 60 mg of N-ethylmorpholine and 118 mg of dicyclohexylcarbodiimide there were obtained, after chromatography on silica gel using 10% methanol in dichloromethane for the elution, 146 mg of N-[2(R)-hydroxy-3(S)-[[N-(1-isoquinolylcarbonyl)-L-asparaginyl]amino]-4-phenylbutyl]-L-proline tert.butyl ester as a pale cream solid from ethyl acetate/n-hexane; MS: m/e 604 [M+H]+.

Sources & evidence

ORD record
ord-2caad1d8d85c4ed6a5965e5aef5bfc9f
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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