4-Methoxy-alpha-toluenethiol → HCID 69076973, compound

HRID 2101215Notes

Reaction equation

HRID 2101215 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][SH:10])=[CH:5][CH:4]=1.[C:11]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH:19]=[C:20]([CH2:28][C:29]2[CH:30]=[N:31][C:32]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:33][CH:34]=2)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:12]=1>>[C:11]1([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH:19]([S:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:20]([CH2:28][C:29]2[CH:30]=[N:31][C:32]([NH:35][C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])=[CH:33][CH:34]=2)[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH:12]=1

Participants

3

Reactant 2

HCID 804074-Methoxy-alpha-toluenethiolHCID 69073585HCID 69073585, compound

Product 1

HCID 69076973HCID 69076973, compoundYield 90%

Procedure

A solution of 4-methoxy-α-toluenethiol (0.58 mL, 4.17 mmol) in dry, degassed DMF (2 mL) was treated at room temperature with a catalytic amount of sodium hydride (60% in mineral oil), followed by a solution of tert-butyl 5-(1,1′-biphenyl-3-yl)-2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)pent-2-enoate (1.073 g, 2.08 mmol) in dry, degassed DMF (5 mL). After 20 h at room temperature the reaction mixture was diluted with EtOAc and washed with water three times. The organic layer was dried Na2SO4), concentrated, and subjected to flash chromatography (heptan/EtOAc, 3:1 and toluene/EtOAc 12:1) to give tert-butyl 5-(1,1′-biphenyl-3-yl)-2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]pentanoate (1.251 g, 90%)

Workup

  1. customdegassed DMF (2 mL)
  2. additionwas treated at room temperature with a catalytic amount of sodium hydride (60% in mineral oil)
  3. customin dry
  4. customdegassed DMF (5 mL)
  5. additionAfter 20 h at room temperature the reaction mixture was diluted with EtOAc
  6. washwashed with water three times
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1fd00bf3904442ed8224441f0b2673ad
Source dataset
uspto-grants-2009_08
Patent number
US07572817B2

Reaction notes

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