HCID 135984350, compound → HCID 136053527, compound

HRID 1660118Notes

Reaction equation

HRID 1660118 reaction equation
C([S:4][CH2:5][CH:6]([CH3:32])[C:7]([N:9]1[CH2:31][CH2:30][CH2:29][C@H:10]1[C:11]([O:13][CH2:14][C:15]1[CH:27]=[C:26]2[N:17]([C:18](=[O:28])[NH:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=32)[N:16]=1)=[O:12])=[O:8])(=O)C>N>[SH:4][CH2:5][CH:6]([CH3:32])[C:7]([N:9]1[CH2:31][CH2:30][CH2:29][C@H:10]1[C:11]([O:13][CH2:14][C:15]1[CH:27]=[C:26]2[N:17]([C:18](=[O:28])[NH:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=32)[N:16]=1)=[O:12])=[O:8]

Participants

3

Reactant 1

HCID 135984350HCID 135984350, compound

Product 1

HCID 136053527HCID 136053527, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A mixture of 4.56 g (0.01 M) of (S)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline, (5,6-dihydro-5-oxopyrazolo[1,5-c]-quinazolin-2-yl)-methyl ester and 200 cc 1.25 N of methanolic ammonia is stirred at room temperature under nitrogen for 2 hours. A clear solution forms after about 10 minutes. The solution is concentrated to dryness at 15 mm and 30° and the residue (4.4 g) dissolved in 250 cc 50% CHCl3 --CH2Cl2, washed with 2×150 cc H2O (to remove acetamide) and dried over MgSO4. The solution is concentrated to yield 3 g (75%) product, m.p. 140°-142° d.

Workup

  1. waitA clear solution forms after about 10 minutes
  2. concentrationThe solution is concentrated to dryness at 15 mm and 30°
  3. dissolutionthe residue (4.4 g) dissolved in 250 cc 50% CHCl3
  4. washCH2Cl2, washed with 2×150 cc H2O (to remove acetamide)
  5. dry with materialdried over MgSO4
  6. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-28da46bf38394a5d99a0154ec33fcb0b
Source dataset
uspto-grants-1981_12
Patent number
US04307099

Reaction notes

Loading…