Acetic Acid → HCID 13454632, compound

HRID 1284954Notes

Reaction equation

HRID 1284954 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][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]([OH:31])=[O:30])[C:24]2[CH:32]=[CH:33][CH:34]=[CH:35][C:23]=2[S:22][CH2:21]1)[C:14]([O:16]CC)=[O:15].C(O)(=O)C.O.CO>[OH-].[Na+]>[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][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]([OH:31])=[O:30])[C:24]2[CH:32]=[CH:33][CH:34]=[CH:35][C:23]=2[S:22][CH2:21]1)[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 962Water2×HCID 13605326HCID 13605326, compound

Product 1

HCID 13454632HCID 13454632, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3(R)-[10-amino-1(S)-ethoxycarboxyldecyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid (0.28 g) obtained in Example 74 in 1N sodium hydroxide (7 ml) stands for 1 hour at room temperature. After addition of acetic acid (2 ml) and water (5 ml), the mixture is subjected to Amberlite XAD-2 column chromatography (methanol:water=1:1). The eluate is concentrated under reduced pressure. The deposited crystal is collected by filtration and dried to yield 3(R)-[10-amino-1(S)-carboxydecyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid (0.12 g).

Workup

  1. concentrationThe eluate is concentrated under reduced pressure
  2. filtrationThe deposited crystal is collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-b76f0d91ebe64f9eb0cf3693f68500a8
Source dataset
uspto-grants-1986_01
Patent number
US04564612

Reaction notes

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