Stannous Chloride → HCID 69881179, compound

HRID 2122026Notes

Reaction equation

HRID 2122026 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([OH:33])[C@@H:11]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N([C@H]([C@H](O)COCC1C=CC=CC=1)C(O)=O)=[N+]=[N-].[Sn](Cl)Cl>CO>[CH2:1]([O:8][CH2:9][C@H:10]([OH:33])[C@@H:11]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 9890928HCID 9890928, compoundHCID 86593656HCID 86593656, compound

Product 1

HCID 69881179HCID 69881179, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2R,3S)-4-Benzyloxy-3-hydroxy-2-(4′-methoxy-biphenyl-4-sulfonylamino)-butyric acid. To a solution of (2R, 3S)-2-azido-4-benzyloxy-3-hydroxy-butyric acid (50 mg) in methanol (1 mL) is added tin (II) chloride (60 mg) and the reaction mixture is stirred at room temperature for 2 hr. The volatiles are removed under vacuum and the residue is dissolved in dioxane-water (1.6 mL, 1:1, v/v). To the mixture is added triethylamine (0.1 mL) and (4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl chloride (110 mg) and the mixture is stirred at room temperature for 10 hr. The volatiles are removed under vacuum and the residue is treated with methanol (3 mL) and acetic acid (1 mL). The precipitate is filtered off, the filtrate is concentrated and a crude product is purified using RF HPLC to give (2R,3R)-4-benzyloxy-3-hydroxy-2-(4′-methoxy-biphenyl-4-sulfonylamino)-butyric acid as a white, crystalline solid.

Workup

  1. customThe volatiles are removed under vacuum
  2. dissolutionthe residue is dissolved in dioxane-water (1.6 mL, 1:1
  3. additionTo the mixture is added triethylamine (0.1 mL) and (4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl chloride (110 mg)
  4. stirringthe mixture is stirred at room temperature for 10 hr
  5. customThe volatiles are removed under vacuum
  6. additionthe residue is treated with methanol (3 mL) and acetic acid (1 mL)
  7. filtrationThe precipitate is filtered off
  8. concentrationthe filtrate is concentrated
  9. customa crude product is purified

Sources & evidence

ORD record
ord-b09fb3f3cc6b44f8b0a062f6f7928e76
Source dataset
uspto-grants-2004_02
Patent number
US06696456B1

Reaction notes

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