2,2-Dimethyl-3-oxazolidinecarboxylate → HCID 178513886, compound

HRID 1657260Notes

Reaction equation

HRID 1657260 reaction equation
CC1(C)[N:6](C([O-])=O)CCO1.C(S(C[C@@H](CC1C=CC=CC=1)C(N[C@H:23]([C:42]([OH:44])=O)[CH2:24][C:25]1[N:29](C2C=CC([N+]([O-])=O)=CC=2[N+]([O-])=O)[CH:28]=[N:27][CH:26]=1)=O)(=O)=O)(C)(C)C>>[NH:27]1[CH:26]=[C:25]([CH2:24][CH2:23][C:42]([NH2:6])=[O:44])[N:29]=[CH:28]1

Participants

3

Reactant 2

HCID 190810462,2-Dimethyl-3-oxazolidinecarboxylateHCID 22845096N-[(S)-alpha-[(t-butylsulphonyl)methyl]hydrocinnamoyl]-3-(2,4-dinitrophenyl)-L-histidine

Product 1

HCID 178513886HCID 178513886, compound

Procedure

In an analogous manner to that described in Example 16, by reacting t-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(R or S)-hydroxy-[(R or S)-tetrahydro-2-furyl]methyl]-2,2-dimethyl-3-oxazolidinecarboxylate with N-[(S)-α-[(t-butylsulphonyl)methyl]hydrocinnamoyl]-3-(2,4-dinitrophenyl)-L-histidine there is obtained (S)-α-[(S)-α-[(t-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3R or S)-1-(cyclohexylmethyl)-2,3-dihydroxy-3-[(R or S)-tetrahydro-2-furyl]propyl]imidazole-4-propionamide in the form of a yellow amorphous powder, MS: 827 (M+H)+. The cleavage of the dinitrophenyl group with thiolactic acid is effected in an analogous manner to Example 13 and yields (S)-α-[(S)-α-[(t-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3R or S)-1-(cyclohexylmethyl)-2,3-dihydroxy-3-[(R or S)-tetrahydro-2-furyl]propyl]imidazole-4-propionamide as a pale yellow amorphous solid, MS: 661 (M+H)+.

Sources & evidence

ORD record
ord-2202347884f94a60bf35fd11353ccfa2
Source dataset
uspto-grants-1993_10
Patent number
US05256645

Reaction notes

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