Ammonium Chloride → (2z)-4-{[Tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl n-(tert-butoxycarbonyl)glycinate

HRID 1375708Notes

Reaction equation

HRID 1375708 reaction equation
[Si:1]([O:8][CH2:9]/[C:10](/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[C:11](/[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)\[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:30]([NH:37][CH2:38][C:39](O)=[O:40])([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].CCN=C=NCCCN(C)C.Cl.[Cl-].[NH4+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:33]([O:32][C:30]([NH:37][CH2:38][C:39]([O:13][CH2:12]/[C:11](/[C:14]1[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=1)=[C:10](/[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)\[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[O:40])=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58787782(2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-ol

Product 1

HCID 58787788(2z)-4-{[Tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl n-(tert-butoxycarbonyl)glycinateYield 98.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 16.4 g of (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methyl-sulfonyl)phenyl]-3-phenylbut-2-en-1-ol, 1.92 g of DMAP and 7.30 g of Boc-Glycine in 125 mL of CH2Cl2 at 0° C. was added 8.0 g of EDCl. The reaction mixture was stirred for 4 h. Then saturated ammonium chloride solution was added and extracted with EtOAc. The organic layer was combined, washed with brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography over silica gel (5–55% EtOAc/hexane) to afford 22 g of the titled compound as a colorless oil. 1H (500 MHz, acetone-d6): δ 7.67 (d, 2H), 7.34 (d, 2H), 7.13–7.04 (m, 5H), 6.26 (br s, NH), 5.23 (s, 2H), 4.76 (s, 2H), 3.73 (d, 2H), 3.02 (s, 3H), 1.40 (s, 9H), 0.81 (s, 9H), −0.01 (s, 6H).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated
  5. customthe residue was purified by flash chromatography over silica gel (5–55% EtOAc/hexane)

Sources & evidence

ORD record
ord-8aa874796c8348618df175811314553b
Source dataset
uspto-grants-2007_01
Patent number
US07169809B2

Reaction notes

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