HCID 13605305, compound → HCID 13605308, compound

HRID 649377Notes

Reaction equation

HRID 649377 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:19][C@@H:20]1[C:26](=[O:27])[N:25]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:24]2[CH:36]=[CH:37][CH:38]=[CH:39][C:23]=2[S:22][CH2:21]1)[C:14]([O:16]CC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[Na+].O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:19][C@@H:20]1[C:26](=[O:27])[N:25]([CH2:28][C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[C:24]2[CH:36]=[CH:37][CH:38]=[CH:39][C:23]=2[S:22][CH2:21]1)[C:14]([OH:16])=[O:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 13605305HCID 13605305, compound

Product 1

HCID 13605308HCID 13605308, compoundYield 64.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

In a mixture of 40 ml of methanol and 25 ml of 1N aqueous sodium hydroxide solution is dissolved 0.6 g of tert-butyl 3(R)-[5-tert-butoxycarbonylamino-1(S)-ethoxycarbonylpentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate as obtaiend in Example 37, and 10 ml of water is further added to the solution, followed by stirring at room temperature for 2 hours. The methanol is evaporated off under reduced pressure, and the residual solution is made weakly acidified with phosphoric acid and extracted with ethyl acetate. The extract is dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 0.37 g of tert-butyl 3(R)-[5-tert-butoxycarbonylamino-1(S)-carboxypentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate as a colorless viscous material. This product is treated with ethyl acetate to yield a colorless crystalline powder, melting at 134°-135° C.

Workup

  1. additionis further added to the solution
  2. customThe methanol is evaporated off under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5c521978052b4c25a472b1c8a3597996
Source dataset
uspto-grants-1988_04
Patent number
US04739066

Reaction notes

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