Hydrochloric Acid → (S)N-(2-mercapto-1-oxo-3-phenylpropyl) D-Tryptophan

HRID 369203

Reaction equation

HRID 369203 reaction equation
Cl.[NH2:2][C@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.N[C@@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1.C([S:40][C@H:41]([CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:42](O)=[O:43])(=O)C1C=CC=CC=1.C(S[C@@H](CC1C=CC=CC=1)C(O)=O)(=O)C1C=CC=CC=1>>[SH:40][CH:41]([CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:42]([NH:2][C@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:43]

Participants

6

Reactant 5

HCID 313Hydrochloric Acid2×HCID 6305L-TryptophanHCID 9060D-TryptophanHCID 9878985(S)-2-(benzoylthio)-3-phenylpropanoic acidHCID 9943761(R)-2-(benzoylthio)-3-phenylpropanoic acid

Product 1

HCID 57125133(S)N-(2-mercapto-1-oxo-3-phenylpropyl) D-Tryptophan

Procedure

The operation is carried out as in Stage 1 of Example 24 using, instead of the hydrochloride of the methyl ester of L-Tryptophan, the hydrochloride of the methyl ester of D-Tryptophan and, instead of (R)-2-(benzoylthio)-3-phenylpropanoic acid, (S)-2-(benzoylthio)-3-phenylpropanoic acid (prepared according the same reference). After purification by chromatography on silica with a methylene chloride-ethyl acetate: 95-5 mixture as eluant, 564 mg of expected product (SR isomer) (colourless foam) is obtained.

Workup

  1. customAfter purification by chromatography on silica with a methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-0fa0366102284a0d975afc5404871b5f
Source dataset
uspto-grants-2000_10
Patent number
US06136842

Linked notes

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