Lithium hydroxide, monohydrate → HCID 12990924, compound

HRID 2120599Notes

Reaction equation

HRID 2120599 reaction equation
C[O:2][C:3](=[O:32])[C@H:4]([NH:12][C:13]([O:15][CH2:16][C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH:21][CH:20]=2)=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[OH-].[Li+]>CO.O>[C:26]1([C:22]2[CH:23]=[C:24]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([CH2:16][O:15][C:13]([NH:12][C@H:4]([CH2:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:3]([OH:32])=[O:2])=[O:14])=[CH:25]3)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12990923HCID 12990923, compound

Product 1

HCID 12990924HCID 12990924, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (R)-2-(5-phenyl-indol-2-ylmethoxycarbonylamino)-3-phenyl-propionic acid methyl ester 46 (0.195 g, 0.455 mmole) in methanol (20 ml) was treated with a solution of lithium hydroxide monohydrate (23 mg, 0.55 mmole) in water (1 ml) and heated to 50° C. for 7 hrs, cooled to room temperature, acidified, evaporated, extracted with EtOAc, washed, dried, and evaporated. The residue was purified by chromatography to give about 46 mg of (R)-2-(5-phenyl-indol-2-ylmethoxycarbonylamino)-3-phenyl-propionic acid 47, mp. 168-174°.

Workup

  1. temperaturecooled to room temperature
  2. customevaporated
  3. extractionextracted with EtOAc
  4. washwashed
  5. customdried
  6. customevaporated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-de81a672ee474336bd4555350ba05230
Source dataset
uspto-grants-2004_02
Patent number
US06693098B2

Reaction notes

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