Hydrochloric Acid → HCID 57264124, compound

HRID 2294742Notes

Reaction equation

HRID 2294742 reaction equation
C([NH:8][C@H:9]([C:13]([OH:15])=O)[CH2:10][S:11][CH3:12])(OC(C)(C)C)=O.[NH2:16][C@@H:17]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]([OH:24])[C@H:19]([CH:21]1[CH2:23][CH2:22]1)[OH:20].Cl>CO>[NH2:8][C@@H:9]([CH2:10][S:11][CH3:12])[C:13]([NH:16][C@@H:17]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]([OH:24])[C@H:19]([CH:21]1[CH2:23][CH2:22]1)[OH:20])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7018744Boc-cys(ME)-OHHCID 14930738(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol

Product 1

HCID 57264124HCID 57264124, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl [(R)-1-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]-2-(methylthio)ethyl]carbamate was obtained as an amorphous solid, MS: 445 (M+H)+, by condensing (R)-Boc-(S-methyl)cysteine (J. Chem. Soc. C 1967, 2632) and (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol in an analogous manner to that described in Example 1g). Subsequent cleavage of the Boc protecting group using hydrochloric acid in methanol yielded (R)-2-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(methylthio)propionamide.

Sources & evidence

ORD record
ord-d7e9321b44484429b78b96e555f9d118
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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