Triethylamine → HCID 67275409, compound

HRID 1696929Notes

Reaction equation

HRID 1696929 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[N:23]=[C:22]3[C:17]([C:18](=[O:38])[C:19]([C:35](O)=[O:36])=[CH:20][N:21]3[CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=3[O:33][CH3:34])=[CH:16][C:15]=2[F:39])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:42](CC)CC)C.ClC(OC(C)=C)=O.[OH-].[NH4+]>ClCCl.C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[N:23]=[C:22]3[C:17]([C:18](=[O:38])[C:19]([C:35]([NH2:42])=[O:36])=[CH:20][N:21]3[CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=3[O:33][CH3:34])=[CH:16][C:15]=2[F:39])[CH2:10]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 93846Isopropenyl chloroformateHCID 67275373HCID 67275373, compound

Product 1

HCID 67275409HCID 67275409, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of EXAMPLE 75B (350 mg) and triethylamine (0.098 mL) in dichloromethane (4 mL) and THF (3 mL) at 0° C. was treated with isopropenyl chloroformate (0.077 mL), stirred for 30 minutes, treated with concentrated ammonium hydroxide (0.100 mL), stirred for 18 hours at ambient temperature, loaded onto a flash silica gel column, and eluted with a methanol/dichloromethane gradient.

Workup

  1. stirringstirred for 18 hours at ambient temperature
  2. washeluted with a methanol/dichloromethane gradient

Sources & evidence

ORD record
ord-d13edb81643740d689792ae94f2d0122
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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