2-Oxo-4-phenylbutyric acid → HCID 18597438, compound

HRID 1981147Notes

Reaction equation

HRID 1981147 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][S:14][CH2:15][CH2:16][C@@H:17]([C:19]([N:21]1[C@H:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)=[O:20])[NH2:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[C:37]([CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:38]([OH:40])=[O:39]>CO>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][S:14][CH2:15][CH2:16][C@@H:17]([C:19]([N:21]1[C@H:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)=[O:20])[NH:18][CH:37]([C:38]([OH:40])=[O:39])[CH2:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 697322-Oxo-4-phenylbutyric acidHCID 18597437HCID 18597437, compound

Product 1

HCID 18597438HCID 18597438, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

S-(2-Benzyloxycarbonylaminoethyl)-N-tert-butoxy-carbonyl-L-homocysteine (2.14 g., 0.00518 mole) and ethyl 1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (1.12 g., 0.00545 mole) were coupled via the procedure described in Example 5 to give 2.24 g. (72%) of ethyl N-[S-(2-benzyloxycarbonylaminoethyl)-N-tert-butoxycarbonyl-L-homocysteinyl]-1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (1); an oil. Compound 1 (1.10 g., 0.00183 mole) was stirred for 50 minutes at room temperature with 25 ml of trifluoroacetate acid. Concentration in vacuo gave ethyl N-[S-(2-benzyloxycarbonylaminoethyl)-L-homocysteinyl]1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (2) as a crude orange oil. This intermediate (2) was reductively alkylated with 2-oxo-4-phenylbutyric acid (3.00 g., 0.0068 mole) according to the procedure described in Example 5. After chromatography on an LH-20 column with methanol, 0.30 g. (25%) of ethyl N-[S-(2-benzyloxycarbonylaminoethyl)-N-(1-carboxy-3-phenylpropyl)-L-homocysteinyl]-1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (3) was obtained; a colorless oil.

Sources & evidence

ORD record
ord-8f3b1759b11c4ccf86a32a7af4b72be8
Source dataset
uspto-grants-1985_04
Patent number
US04512979

Reaction notes

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