Methyl 3-(2-amino-2-methylpropyl)benzoate → (R)-Methyl 3-[2-[[2-[4-(benzyloxy)-3-[[(tert-butyldimethylsilyl)oxy]methyl]phenyl]-2-[(tert-butyldimethylsilyl)oxy]ethyl]amino]-2-methylpropyl]benzoate

HRID 385274Notes

Reaction equation

HRID 385274 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:16]Br)=[CH:11][C:10]=1[CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:35][C:36]([CH3:49])([CH3:48])[CH2:37][C:38]1[CH:39]=[C:40]([CH:45]=[CH:46][CH:47]=1)[C:41]([O:43][CH3:44])=[O:42]>CCN(CC)CC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:16][NH:35][C:36]([CH3:49])([CH3:48])[CH2:37][C:38]2[CH:39]=[C:40]([CH:45]=[CH:46][CH:47]=2)[C:41]([O:43][CH3:44])=[O:42])=[CH:11][C:10]=1[CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 57516949Methyl 3-(2-amino-2-methylpropyl)benzoateHCID 58505282(R)-[1-[4-(Benzyloxy)-3-[[(tert-butyldimethylsilyl)oxy]methyl]phenyl]-2-bromoethoxy](tert-butyl)dimethylsilane

Product 1

HCID 86659065(R)-Methyl 3-[2-[[2-[4-(benzyloxy)-3-[[(tert-butyldimethylsilyl)oxy]methyl]phenyl]-2-[(tert-butyldimethylsilyl)oxy]ethyl]amino]-2-methylpropyl]benzoateYield 37%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Intermediate 6 (1.6 g, 2.89 mmol) and Intermediate 19 (900 mg, 4.3 mmol) were heated neat at 95° C. for 3 days. The reaction mixture was cooled then chromatography (3:1 Hexanes/EtOAc, 0.1% Et3N) afforded the title compound (730 mg, 37%). ES/MS calcd. for C40H62NO5Si2+ 692.4. found m/z=692.4 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled

Sources & evidence

ORD record
ord-660776cfd68a4adcbc723e29f00614c3
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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