Tetrahydrofuran → HCID 12990923, compound

HRID 1827986Notes

Reaction equation

HRID 1827986 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11]([CH2:16][OH:17])=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:18]=[C:19]=[O:20].[CH3:21][O:22][C:23](=[O:33])[C@H:24]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)N.C1COCC1>C(N(CC)CC)C>[CH3:21][O:22][C:23](=[O:33])[C@H:24]([NH:18][C:19]([O:17][CH2:16][C:11]1[NH:12][C:13]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH:15][CH:14]=2)=[O:20])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 22062805HCID 22062805, compoundHCID 86584107HCID 86584107, compound

Product 1

HCID 12990923HCID 12990923, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of (5-phenyl-indol-2-yl)-methanol 45 (0.259 g, 1.16 mmole), (R)-2-isocyanato-3-phenyl-propionic acid methyl ester 5 (0.286 g, 1.39 mmole), in triethylamine (0.37 ml), and THF (10 ml) was heated to 50° C. under a nitrogen atmosphere for 22 hrs. The solvent was evaporated and the residue was purified by chromatography to give about 0.220 g of (R)-2-(5-phenyl-indol-2-ylmethoxycarbonylamino)-3-phenyl-propionic acid methyl ester 46, mp. 142–143° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-0a43c5ac1fdd439784e0e5b2883f1e44
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

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