Hydrogen Bromide → HCID 18597442, compound

HRID 1981148Notes

Reaction equation

HRID 1981148 reaction equation
C(OC([NH:11][CH2:12][CH2:13][S:14][CH2:15][CH2:16][C@@H:17]([C:31]([N:33]1[C@H:42]([C:43]([O:45]CC)=[O:44])[CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34]1)=[O:32])[NH:18][CH:19]([C:28]([OH:30])=[O:29])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O)C1C=CC=CC=1.Br>C(O)(=O)C>[NH2:11][CH2:12][CH2:13][S:14][CH2:15][CH2:16][C@@H:17]([C:31]([N:33]1[C@H:42]([C:43]([OH:45])=[O:44])[CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34]1)=[O:32])[NH:18][CH:19]([C:28]([OH:30])=[O:29])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 18597438HCID 18597438, compound

Product 1

HCID 18597442HCID 18597442, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 3 was then hydrolyzed with 30% hydrogen bromide in glacial acetic acid. After purification over LH-20 with methanol, 0.054 g. (25%) of N-[S-(2-aminoethyl)-N-(1-carboxy-3-phenylpropyl)-L-homocysteinyl]-1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylic acid was obtained; a white solid after freeze drying; nmr (CO3OD): δ2.1-2.25 (m, 4H, aromatic CH2CH2 --, --SCH2CH2CH<), 2.7-2.9 (m, 8H, aromatic CH2CH2 --, aromatic CH2CH<--CH2S--CH2 --), 3.0-3.25 (m, 2H, --SCH2CH2NH2), 3.32 (S, 2H, aromatic CH2N<), 3.5-3.8 (m, 1H, NCHRCO2 --), 7.2.-7.3 (m, 4H, aromatic), ms: M+ 463.

Workup

  1. customAfter purification over LH-20 with methanol, 0.054 g

Sources & evidence

ORD record
ord-06763e9dee514966aa5bf325776d584d
Source dataset
uspto-grants-1985_04
Patent number
US04512979

Reaction notes

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