Tert-butyl[(2,5-difluoro-4-isocyanatobenzyl)oxy]dimethylsilane → N,N'-Diisopropylethylenediamine

HRID 630424Notes

Reaction equation

HRID 630424 reaction equation
[C:1]([Si:5]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([N:17]=[C:18]=[O:19])=[CH:12][C:11]=1[F:20])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[OH:21][CH2:22][CH2:23][N:24]([CH3:46])[C@H:25]1[CH2:30][CH2:29][C@H:28]([O:31][C:32]([C:41]2[S:42][CH:43]=[CH:44][CH:45]=2)([C:36]2[S:37][CH:38]=[CH:39][CH:40]=2)[C:33]([O-:35])=[O:34])[CH2:27][CH2:26]1>>[C:1]([Si:5]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([N:17]=[C:18]=[O:19])=[CH:12][C:11]=1[F:20])([CH3:7])[CH3:6])([CH3:4])([CH3:2])[CH3:3].[OH:21][CH2:22][CH2:23][N:24]([CH3:46])[C@H:25]1[CH2:30][CH2:29][C@H:28]([O:31][C:32]([C:36]2[S:37][CH:38]=[CH:39][CH:40]=2)([C:41]2[S:42][CH:43]=[CH:44][CH:45]=2)[C:33]([O-:35])=[O:34])[CH2:27][CH2:26]1.[CH:25]([NH:24][CH2:23][CH2:18][NH:17][CH:13]([CH3:12])[CH3:14])([CH3:30])[CH3:26]

Participants

5

Reactant 2

HCID 87411319Tert-butyl[(2,5-difluoro-4-isocyanatobenzyl)oxy]dimethylsilaneHCID 178484574HCID 178484574, compound

Product 3

HCID 77628N,N'-DiisopropylethylenediamineHCID 87411319Tert-butyl[(2,5-difluoro-4-isocyanatobenzyl)oxy]dimethylsilaneHCID 178484574HCID 178484574, compound

Procedure

Obtained as a colorless oil (41%) from tert-butyl[(2,5-difluoro-4-isocyanatobenzyl)oxy]dimethylsilane (intermediate 141; 0.43 g, 1.46 mmol), trans-4-[(2-hydroxyethyl)(methyl)amino]cyclohexylhydroxy(di-2-thienyl)acetate (intermediate 60; 0.57 g, 1.46 mmol) and diisopropylethylendiamine (0.38 mL, 2.22 mmol) following the experimental procedure as described in intermediate 61 (reaction time and temperature: 24 hours at 60° C.), followed by a purification by column chromatography with silica gel, eluting with methylene chloride/ethanol (9:1).

Sources & evidence

ORD record
ord-03c2938df66f4012baa5d7f335399121
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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