Triethylamine → 1-[3-(4-Bromobenzoyl)propionyl]-L-proline methyl ester

HRID 903441Notes

Reaction equation

HRID 903441 reaction equation
[CH2:1](N(CC)CC)C.[Br:8][C:9]1[CH:21]=[CH:20][C:12]([C:13]([CH2:15][CH2:16][C:17]([OH:19])=O)=[O:14])=[CH:11][CH:10]=1.Cl.C[N:24]1[CH2:31][CH2:30][CH2:29][C@H:25]1[C:26]([OH:28])=[O:27]>C(#N)C>[CH3:1][O:28][C:26](=[O:27])[C@@H:25]1[CH2:29][CH2:30][CH2:31][N:24]1[C:17](=[O:19])[CH2:16][CH2:15][C:13](=[O:14])[C:12]1[CH:11]=[CH:10][C:9]([Br:8])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 806463-(4-Bromobenzoyl)propionic acidHCID 665999121-Methyl-L-proline hydrochloride

Product 1

HCID 228124471-[3-(4-Bromobenzoyl)propionyl]-L-proline methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The procedure of Example 28 is repeated, using 21.8 ml. of triethylamine in place of the diisopropylethylamine and using 27.3 g. of 3-(4bromobenzoyl)propionic acid, hydroxysuccinimide ester 13.0 g. of methylproline hydrochloride and 150 ml. of acetonitrile. The desired product is recovered as 16.6 g. of white crystals, m.p. 83°-85° C.

Workup

  1. customThe desired product is recovered as 16.6 g

Sources & evidence

ORD record
ord-d0482ff930ee4bfa9344035fd595597e
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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