Methanol → HCID 13657318, compound

HRID 1731960Notes

Reaction equation

HRID 1731960 reaction equation
[C:1]([NH:9][CH:10]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:11](=[O:30])[CH2:12][CH2:13][N:14]([CH3:29])[C:15]([N:17]1[CH2:28][CH2:27][CH2:26][C@H:18]1[C:19]([O:21]C(C)(C)C)=[O:20])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCC[C@H]1C(O)=O.CO>C(Cl)(Cl)Cl.CO.C(O)(=O)C>[C:1]([NH:9][CH:10]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:11](=[O:30])[CH2:12][CH2:13][N:14]([CH3:29])[C:15]([N:17]1[CH2:28][CH2:27][CH2:26][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 145742L-ProlineHCID 14129891HCID 14129891, compound

Product 1

HCID 13657318HCID 13657318, compound

Reagents, catalysts & solvents 1

HCID 21866353chloroform methanol HOAcSolvent

Procedure

The t-butyl ester product from part (d) (300 mg.) is treated for 1.5 hours with 3 ml. of trifluoroacetic acid, concentrated in vacuo and triturated to a solid with ether/hexane to give 250 mg. of (±)-1-[[[4-benzoylamino)-3-oxo-5-phenylpentyl]methylamino]carbonyl]-L-proline; m.p. 38°-68°; [α]D23 =-9.16° (c=1.2, methanol); Rf =0.71 [silica gel, chloroform:methanol:acetic acid (9:0.5:0.5)].

Workup

  1. concentrationof trifluoroacetic acid, concentrated in vacuo
  2. customtriturated to a solid with ether/hexane
  3. customto give 250 mg

Sources & evidence

ORD record
ord-9919e5c71b8341be913514342996a6de
Source dataset
uspto-grants-1986_11
Patent number
US04623729

Reaction notes

Loading…