tert-Butyl 3-ethynylphenylcarbamate → 2-(Trimethylsilyl)ethyl {1-[2-({3-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)-4-nitrophenyl]pyrrolidin-3-yl}carbamate

HRID 541962

Reaction equation

HRID 541962 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:25])[O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:12]1.[C:26]([C:28]1[CH:29]=[C:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH:31]=[CH:32][CH:33]=1)#[CH:27]>>[C:37]([O:36][C:35]([NH:34][C:30]1[CH:29]=[C:28]([C:26]#[C:27][C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=2[N:11]2[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:25])[O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:12]2)[CH:33]=[CH:32][CH:31]=1)=[O:41])([CH3:40])([CH3:39])[CH3:38]

Participants

3

Reactant 2

HCID 11275982tert-Butyl 3-ethynylphenylcarbamateHCID 668797292-(Trimethylsilyl)ethyl [1-(2-bromo-4-nitrophenyl)pyrrolidin-3-yl]carbamate

Product 1

HCID 866363032-(Trimethylsilyl)ethyl {1-[2-({3-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)-4-nitrophenyl]pyrrolidin-3-yl}carbamateYield 91%

Procedure

The desired compound was prepared according to the procedure of Example A11, step C, using 2-(trimethylsilyl)ethyl [1-(2-bromo-4-nitrophenyl)pyrrolidin-3-yl]carbamate and tert-butyl (3-ethynylphenyl)carbamate as the starting materials in 91% yield. LCMS for C29H39N4O6Si (M+H)+: m/z=567.2.

Sources & evidence

ORD record
ord-0db4fc9ce6ec44cca7e5d24e1b2d1d02
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Linked notes

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