HCID 57081244, compound → HCID 57189995, compound

HRID 1252520Notes

Reaction equation

HRID 1252520 reaction equation
C[O:2][C:3]([C@@H:5]([NH:16][C@H:17]([CH3:43])[C@H:18]([NH:23]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:19]([O:21]C)=[O:20])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:4]>CO.Cl>[NH2:23][C@@H:18]([C@H:17]([NH:16][C@H:5]([C:3]([OH:4])=[O:2])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[CH3:43])[C:19]([OH:21])=[O:20]

Participants

4

Reactant 1

HCID 57081244HCID 57081244, compound

Product 1

HCID 57189995HCID 57189995, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of methyl (2S,3R)-3-[[(1S)-1-methoxycarbonyl-2-(3-indolyl)ethyl]amino]-2-tritylaminobutyrate (600 mg) in a mixture of methanol (10 ml) and 1N hydrochloric acid (2 ml) was stirred for 1 hour at room temperature and methanol was evaporated in vacuo. The residual aqueous solution was washed with chloroform and diluted with water (15 ml). To the solution was added sodium hydroxide (500 mg) and the mixture was stirred overnight at room temperature. The mixture was adjusted to pH 3 with 1N hydrochloric acid and the solution was subjected to a column of Dowex 50W x 8 (H+, 20 ml). The column was washed with water and the elution was carried out with 1.4% aqueous ammonia. The object fractions were collected and lyophilized to give (2S,3R)-2-amino-3-[[(1S)-1-carboxy-2-(3-indolyl)ethyl]amino]butyric acid (260 mg) as a white powder.

Workup

  1. custommethanol was evaporated in vacuo
  2. washThe residual aqueous solution was washed with chloroform
  3. additiondiluted with water (15 ml)
  4. additionTo the solution was added sodium hydroxide (500 mg)
  5. stirringthe mixture was stirred overnight at room temperature
  6. washThe column was washed with water
  7. washthe elution
  8. customThe object fractions were collected

Sources & evidence

ORD record
ord-3a58f9ffc46444188363785a7667f0ca
Source dataset
uspto-grants-1988_05
Patent number
US04743614

Reaction notes

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