4-Methylmorpholine → 4-(Hydroxymethyl)-N-{2-[(triphenylmethyl)sulfanyl]ethyl}benzamide

HRID 2221122Notes

Reaction equation

HRID 2221122 reaction equation
[C:1]([S:20][CH2:21][CH2:22][NH2:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([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.FC1C([O:31][C:32](=O)[C:33]2[CH:38]=[CH:37][C:36]([CH2:39][OH:40])=[CH:35][CH:34]=2)=C(F)C(F)=C(F)C=1F.CN1CCOCC1>ClCCl>[OH:40][CH2:39][C:36]1[CH:37]=[CH:38][C:33]([C:32]([NH:23][CH2:22][CH2:21][S:20][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:31])=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 262764S-TritylcysteamineHCID 53413280Pentafluorophenyl 4-(hydroxymethyl)benzoate

Product 1

HCID 597106244-(Hydroxymethyl)-N-{2-[(triphenylmethyl)sulfanyl]ethyl}benzamideYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of S-trityl cysteamine (1.60 g, 5.00 mmol) and 4-hydroxymethylbenzoic acid pentafluorophenyl ester (MilliGen, 1.51 g, 5.00 mmol) in dichloromethane (40 ml) was added N-methylmorpholine (0.55 ml, 5.0 mmol). The mixture was stirred at room temperature for 36 hrs. Precipitated material was filtered off, washed with dichloromethane and dried to give 1.30 g (57%) of white solid. NMR analysis was in accordance with the structure.

Workup

  1. filtrationPrecipitated material was filtered off
  2. washwashed with dichloromethane
  3. customdried

Sources & evidence

ORD record
ord-770f1b3421934867a1061fa4ff7a88ea
Source dataset
uspto-grants-2008_05
Patent number
US07368474B2

Reaction notes

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