Hydrochloric Acid → HCID 86596959, compound

HRID 2225281Notes

Reaction equation

HRID 2225281 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18]C(=O)OC(C)(C)C)[CH2:14][C@H:13]1[CH2:26][S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(OCC)(=O)C.O1CCOCC1>[NH2:18][C@@H:15]1[CH2:16][CH2:17][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:13]([CH2:26][S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])[CH2:14]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90994183HCID 90994183, compound

Product 1

HCID 86596959HCID 86596959, compoundYield 114.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl(1R,3R,4S)-4-benzyloxycarbonylamino-3-(isopropylsulfonylmethyl)cyclohexylcarbamate (111 mg) in ethyl acetate (4 mL) was treated with a solution of HCl in dioxane (4.0 M, 4 mL). The mixture was stirred at rt for 50 min, then was concentrated to provide the hydrochloride salt of benzyl (1S,2R,4R)-4-amino-2-(isopropylsulfonylmethyl)cyclohexylcarbamate (100 mg) as a white glassy solid. MS found: (M+H)+=369.2.

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-9d73f2406ab544eeb51d6b4092e5a213
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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