Acetic Acid → HCID 13454630, compound

HRID 1284952Notes

Reaction equation

HRID 1284952 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]([NH:16][C@@H:17]1[C:23](=[O:24])[N:22]([CH2:25][C:26]([OH:28])=[O:27])[C:21]2[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=2[S:19][CH2:18]1)[C:11]([O:13]CC)=[O:12].C(O)(=O)C.O>[OH-].[Na+]>[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]([NH:16][C@@H:17]1[C:23](=[O:24])[N:22]([CH2:25][C:26]([OH:28])=[O:27])[C:21]2[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=2[S:19][CH2:18]1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 13454628HCID 13454628, compound

Product 1

HCID 13454630HCID 13454630, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3(R)-[7-amino-1(S)-ethoxycarbonylheptyl]amino-4oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid dihydrochloride (0.16 g) obtained in Example 72 in 1N sodium hydroxide (4 ml) is allowed to stand for 30 minutes at room temperature. After addition of acetic acid (2 ml) and water (5 ml), the mixture is submitted to Amberlite XAD-2 column chromatography eluting with methanol-water (1:1). The eluate is concentrated under reduced pressure and lyophilized to yield 3(R)-[7-amino-1(S)-carboxyheptyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid (0.11 g) as a colorless powder.

Workup

  1. washeluting with methanol-water (1:1)
  2. concentrationThe eluate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-b0ac78760dc24faaab8402939ce0b2ba
Source dataset
uspto-grants-1986_01
Patent number
US04564612

Reaction notes

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