2-Methoxyethyl chloroformate → 3-(4-(3(S)-(2-Methoxyethoxycarbonylamino)pyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one

HRID 8169Notes

Reaction equation

HRID 8169 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([NH:6][CH2:7][C@@H:8]2[O:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:24][CH2:23][C@H:22]([NH:25]C(=O)C)[CH2:21]4)=[C:16]([F:29])[CH:15]=3)[CH2:9]2)=[N:2]1.Cl.O1CCNC1=O.Cl[C:38]([O:40][CH2:41][CH2:42][O:43][CH3:44])=[O:39]>>[CH3:44][O:43][CH2:42][CH2:41][O:40][C:38]([NH:25][C@H:22]1[CH2:23][CH2:24][N:20]([C:17]2[CH:18]=[CH:19][C:14]([N:10]3[CH2:9][C@H:8]([CH2:7][NH:6][C:3]4[CH:4]=[CH:5][O:1][N:2]=4)[O:12][C:11]3=[O:13])=[CH:15][C:16]=2[F:29])[CH2:21]1)=[O:39]

Participants

4

Reactant 3

HCID 694002-Methoxyethyl chloroformateHCID 19037880Oxazolidin-2-one hydrochloride saltHCID 207257105(S)-Isoxazol-3-ylaminomethyl-3-(4-(3(S)-acetamidopyrrolidin-1-yl)-3-fluorophenyl)oxazolidin-2-one

Product 1

HCID 695848763-(4-(3(S)-(2-Methoxyethoxycarbonylamino)pyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one

Procedure

Using essentially the method for the intermediate of Example 12, starting from 3-(4(3(S)-aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (419 mg, 0.73 mM) and 2-methoxyethyl chloroformate (450 mg, 3.27 mM) gave the title compound (442 mg).

Sources & evidence

ORD record
ord-23028e4a040e4c08b0b8bcec767ce4a0
Source dataset
uspto-grants-2006_08
Patent number
US07087629B2

Reaction notes

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