Benzyl Alcohol → HCID 86753469, compound

HRID 1458960Notes

Reaction equation

HRID 1458960 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C@@H:11]([CH2:15][NH2:16])[C:12]([OH:14])=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:18](O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([OH:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1.O>C1C=CC=CC=1>[C:19]1([CH3:18])[C:24]([S:33]([OH:36])(=[O:35])=[O:34])=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:37]([O:13][C:12](=[O:14])[C@@H:11]([NH:10][S:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:17])=[CH:6][CH:5]=1)(=[O:8])=[O:9])[CH2:15][NH2:16])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 15589163-Amino-N-((4-methylphenyl)sulfonyl)-L-alanine

Product 1

HCID 86753469HCID 86753469, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

14-3 (5.0 g, 19.4 mmol) was suspended in 150 ml anhydrous benzene along with benzyl alcohol (10 ml, 97 mmol), and p-toluene sulfonic acid mono hydrate (3.87 g, 20.4 mmol). The mixture was refluxed until the theoretical amount of water had collected in a Dean-Stark trap (8.5 h). The resulting solution was cooled and 100 ml anhydrous ether added giving 14-6 as a white solid. 1H NMR (300 MHz, CD3OD) δ7.81 (d, J=8.5 Hz, 2H), 7.71 (d, J=8.5 Hz, 2H), 7.43 (d, J=8.5 Hz, 2H), 7.31 (d, J=8.5 Hz, 2H), 7.28 (m, 5H); 4.98 (m, 2H), 3.91 (m, 1H), 2.89 (m, 2H), 2.35 (s, 3H), 2.31 (s, 2H). ##STR135##

Workup

  1. customhad collected in a Dean-Stark trap (8.5 h)
  2. temperatureThe resulting solution was cooled
  3. addition100 ml anhydrous ether added

Sources & evidence

ORD record
ord-042b308a6458420d9618d56932bc9e9c
Source dataset
uspto-grants-1998_12
Patent number
US05852045

Reaction notes

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