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

HRID 274776Notes

Reaction equation

HRID 274776 reaction equation
CC1(C)[N:6](C([O-])=O)CCO1.[N+](C1C=C([N+]([O-])=O)C=CC=1[N:23]1[C:27]([CH2:28][C@@H:29]([C:31]([OH:33])=O)N)=[CH:26][N:25]=[CH:24]1)([O-])=O>>[NH:25]1[CH:26]=[C:27]([CH2:28][CH2:29][C:31]([NH2:6])=[O:33])[N:23]=[CH:24]1

Participants

3

Reactant 2

HCID 190810462,2-Dimethyl-3-oxazolidinecarboxylateHCID 867484603-(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 dinitropheyl group with thiolactic acid is effected in an analogous manner to Example 13 and yields (S)-α-[(S)-α-[(t-butylsulphonyl)methyl]hudrocinnamamido]-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-cc5265a5037c4ef980b7f4c6a02441c3
Source dataset
uspto-grants-1995_02
Patent number
US05389616

Reaction notes

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