Hydrochloric Acid → (S)-(1-(2-amino-3-hydroxypropanoyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-(trifluoromethyl)phenylcarbamate

HRID 655954Notes

Reaction equation

HRID 655954 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:43])[O:11][CH2:12][C:13]2([C:32](=[O:42])[NH:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[Cl:41])[CH2:18][CH2:17][N:16]([C:19](=[O:31])[C@@H:20]([NH:23]C(OC(C)(C)C)=O)[CH2:21][OH:22])[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.Cl.O1CCOCC1>CO>[F:45][C:2]([F:1])([F:44])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:43])[O:11][CH2:12][C:13]2([C:32](=[O:42])[NH:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[Cl:41])[CH2:18][CH2:17][N:16]([C:19](=[O:31])[C@@H:20]([NH2:23])[CH2:21][OH:22])[CH2:15][CH2:14]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59778634(S)-(1-(2-(tert-butoxycarbonyl)amino-3-hydroxypropanoyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-(trifluoromethyl)phenylcarbamate

Product 1

HCID 59778460(S)-(1-(2-amino-3-hydroxypropanoyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-(trifluoromethyl)phenylcarbamateYield 106.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-(1-(2-(tert-butoxycarbonyl)amino-3-hydroxypropanoyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-(trifluoromethyl)phenylcarbamate (145 mg, 0.22 mmol) in CH3OH (1 mL) was added 4M HCl in dioxane (200 μL, 0.8 mmol, 3.6 equiv.), which was stirred for 2 h. The reaction mixture was concentrated to dryness by co-evaporating with toluene to give (S)-(1-(2-amino-3-hydroxypropanoyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-(trifluoromethyl)phenylcarbamate (130 mg, quant.). LRMS (M+H+) m/z 557.1.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness by co-evaporating with toluene

Sources & evidence

ORD record
ord-91699c7b1afb42c8a27ef0375b959929
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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