Methyl chloroformate → HCID 69981530, compound

HRID 1167461Notes

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][O:20][C:21]4[CH:25]=[CH:24][O:23][N:22]=4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4][CH2:3]1.Cl[C:29]([O:31][CH3:32])=[O:30]>>[CH3:32][O:31][C:29]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][O:20][C:21]4[CH:25]=[CH:24][O:23][N:22]=4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4][CH2:3]1)=[O:30]

Participants

Reactant 2

HCID 6586Methyl chloroformate

HCID 54214185HCID 54214185, compound

Product 1

HCID 69981530HCID 69981530, compoundYield 43.6%

Procedure

Using essentially the technique of Example 94, starting with 3-(4-(4-aminopiperidin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (249 mg, 0.66 mmol) and methyl chloroformate (70 mg, 0.74 mmol) in place of methanesulfonyl choride, gave the desired product (125 mg) after chromatography.

Sources & evidence

ORD record: ord-8d0798eb543943538a6da43df8ea0318
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617339B1

Reaction notes

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