L-Hydroxyproline → (2R,11aS)-6-chloro-1,2,3,11a-tetrahydro-2-hydroxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

HRID 223334

Reaction equation

HRID 223334 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[NH:12][C:11](=[O:13])[O:10][C:8](=O)[C:7]=12.[CH2:14]1[C@@H:18](C(O)=O)[NH:17][CH2:16][C@@H:15]1[OH:22]>CS(C)=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:10])[N:17]3[CH2:16][C@H:15]([OH:22])[CH2:14][C@H:18]3[C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5810L-HydroxyprolineHCID 6390585-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 53899318(2R,11aS)-6-chloro-1,2,3,11a-tetrahydro-2-hydroxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

37.0 g (187.3 mmol) of 6-chloroisatoic acid anhydride and 24.6 g (187.3 mmol) of L-4-hydroxyproline in 180 ml of dimethyl sulphoxide is heated to 100° for 2 hours, evaporated to dryness in a high vacuum and the residue obtained is heated to 130° for 2 hours. By recrystallization from ethanol there is obtained (2R,11aS)-6-chloro-1,2,3,11a-tetrahydro-2-hydroxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione of melting point 284°-287°.

Workup

  1. customevaporated to dryness in a high vacuum
  2. customthe residue obtained
  3. temperatureis heated to 130° for 2 hours
  4. customBy recrystallization from ethanol

Sources & evidence

ORD record
ord-367ff24251fb4fc488f0ead78d9b8186
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Linked notes

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