Water → HCID 13823431, compound

HRID 982551Notes

Reaction equation

HRID 982551 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[S:12][CH:13]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH:14]([OH:18])[C:15](O)=[O:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C(C)=CC=CC=1>[OH:18][CH:14]1[CH:13]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[S:12][C:3]2[C:4]3[C:9]([CH:10]=[CH:11][C:2]=2[NH:1][C:15]1=[O:16])=[CH:8][CH:7]=[CH:6][CH:5]=3

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 9842268HCID 9842268, compound

Product 1

HCID 13823431HCID 13823431, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 1.0g (0.0027 mol) of (-)-β-[(2-amino-1-naphthalenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid and 0.1 g of p-toluenesulfonic acid in 50 ml of xylene was stirred and heated at reflux for 1.5 hours using a Dean-Stark water strap. After cooling the crystals were collected to provide 0.80 g (80%) of [2R-(2α,3α)] 2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,2-b] [1.4]thiazepin-4(5H)-one, mp 238-239°, [α]D 25 -22.97° (C 0.51, acetone).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. temperatureAfter cooling the crystals
  4. customwere collected

Sources & evidence

ORD record
ord-906a723bac634f83acad4ba2c0ab5c61
Source dataset
uspto-grants-1991_02
Patent number
US04996352

Reaction notes

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