Allyl bromide → (R)-N-allyl-4-(3-(tert-butyldiphenylsilyloxy)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

HRID 77284Notes

Reaction equation

HRID 77284 reaction equation
[Si:1]([O:18][C@@H:19]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([NH:33][C:34]3[S:35][CH:36]=[CH:37][N:38]=3)(=[O:32])=[O:31])=[CH:26][CH:25]=2)[C:20]1=[O:39])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:40](N(CC)C(C)C)([CH3:42])[CH3:41].C(Br)C=C>C(Cl)Cl>[CH2:42]([N:33]([C:34]1[S:35][CH:36]=[CH:37][N:38]=1)[S:30]([C:27]1[CH:28]=[CH:29][C:24]([N:21]2[CH2:22][CH2:23][C@@H:19]([O:18][Si:1]([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:20]2=[O:39])=[CH:25][CH:26]=1)(=[O:31])=[O:32])[CH:40]=[CH2:41]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 53627646HCID 53627646, compound

Product 1

HCID 53627647(R)-N-allyl-4-(3-(tert-butyldiphenylsilyloxy)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesized according to General procedure 5. The reaction was set up with (R)-4-(3-(tert-butyldiphenylsilyloxy)-2-oxopyrrolidin-1-yl)-N-(thiazol-2 yl)benzene-sulfonamide (50.0 g, 86.6 mmol), CH2Cl2 (200 mL), N,N-diisopropylethylamine (30.2 mL, 173.2 mmol), and allylbromide (15.0 mL, 173.2 mmol). The residue was purified via silica gel using 50% EtOAc in hexanes to give the desired sulfonamide as a white solid (45.0 g, 72.7 mmol, 84% yield). 1H NMR (400 MHz, DMSO-d6) δ. 7.85-7.79 (m, 6H), 7.70 (dd, J=1.6, 7.7 Hz, 2H), 7.49-7.40 (m, 6H), 7.36 (d, J=4.7 Hz, 1H), 6.93 (d, J=4.7 Hz, 1H), 5.90-5.82 (m, 1H), 5.16 (dd, J=1.3, 10.3 Hz, 1H), 4.97 (d, J=1.3 Hz, 1H), 4.56-4.52 (m, 3H), 3.76-3.72 (m, 1H), 3.56-3.48 (m, 1H), 2.28-2.25 (m, 1H), 2.19-1.98 (m, 1H), 1.11 (s, 9H).

Workup

  1. customSynthesized
  2. customThe residue was purified via silica gel using 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-8a27ced0636c4c1baf7daa3b512ea071
Source dataset
uspto-grants-2014_09
Patent number
US08841282B2

Reaction notes

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