Methyl chloroformate → HCID 52919656, compound

HRID 1423208Notes

Reaction equation

HRID 1423208 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:37]([O:39][CH3:40])=[O:38]>>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[C:37]([O:39][CH3:40])=[O:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 58188985HCID 58188985, compound

Product 1

HCID 52919656HCID 52919656, compoundYield 49%

Procedure

Prepared using the same procedure described in Example 89 from (S)-3-benzyl-1-(3-cyclobutoxy-4-methoxy-phenyl)-piperazine (188 mg, 0.535 mmol), diisopropylethylamine (200 μL, 1.15 mmol), and methyl chloroformate (62 μL, 0.81 mmol) to afford the title compound as a yellow solid (107 mg, 49%). LC/MS (Method B) 4.17 min, [M+1]+ 411.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-81669ff2ca0e41929937557559a5e4f8
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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