Hydrochloric Acid → HCID 178455632, compound

HRID 1609217Notes

Reaction equation

HRID 1609217 reaction equation
[CH2:1]([S:5]([N:8]([C@H:27]([C:29]([O:31]C(C)(C)C)=[O:30])[CH3:28])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[NH:26][N:25]=[N:24][N:23]=2)=[CH:12][CH:11]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].Cl>C(O)(=O)C>[CH2:1]([S:5]([N:8]([C@H:27]([C:29]([OH:31])=[O:30])[CH3:28])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[NH:26][N:25]=[N:24][N:23]=2)=[CH:14][CH:15]=1)(=[O:6])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178455633HCID 178455633, compound

Product 1

HCID 178455632HCID 178455632, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

750 mg of (S)-N-butanesulfonyl-N-(1-tert.-butoxycarbonylethyl)-N-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine are treated for 24 hours at 0° with a solution of hydrogen chloride in glacial acetic acid (1.9N). Evaporation of the mixture and flash-chromatography of the residue (100 g of silica gel; CH2Cl2 /ethyl acetate/toluene/formic acid=40:40:20:4) yields the (S)-N-butanesulfonyl-N-(1-carboxyethyl)-N-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine in the form of a white amorphous powder [m.p.: 90° (decomposition at 127°)].

Workup

  1. customEvaporation of the mixture and flash-chromatography of the residue (100 g of silica gel; CH2Cl2 /ethyl acetate/toluene/formic acid=40:40:20:4)

Sources & evidence

ORD record
ord-238515511d8041f1a40ce4bfa8ca5585
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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