Dichloromethane → L-methionine, N-[1-(2-(biphenyl-4-yl)-2-oxoethyl)-L-prolyl] benzylamide

HRID 2293380Notes

Reaction equation

HRID 2293380 reaction equation
[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][C:4]([C:7](=[O:17])[CH2:8][N:9]2[CH2:16][CH2:15][CH2:14][C@H:10]2[C:11](O)=[O:12])=[CH:3][CH:2]=1.C(N1CCOCC1)C.ClCCl.[CH2:35]([NH:42][C:43](=[O:50])[C@H:44]([CH2:46][CH2:47][S:48][CH3:49])[NH2:45])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(#N)C>[C:1]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:2]=[CH:3][C:4]([C:7](=[O:17])[CH2:8][N:9]2[CH2:16][CH2:15][CH2:14][C@H:10]2[C:11]([N:42]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:43](=[O:50])[C@H:44]([CH2:46][CH2:47][S:48][CH3:49])[NH2:45])=[O:12])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7525EthylmorpholineHCID 18658243L-methionine benzylamideHCID 22878946N-[2-(biphenyl-4-yl)-2-oxoethyl] L-proline

Product 1

HCID 67621280L-methionine, N-[1-(2-(biphenyl-4-yl)-2-oxoethyl)-L-prolyl] benzylamideYield 38.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-[2-(biphenyl-4-yl)-2-oxoethyl] L-proline (54 mg, 0.17 mmol, 1.0 eq), N-ethylmorpholine (133 uL, 1.04 mmol, 6 eq) in acetonitrile (0.5 mL) was cooled to 0° C. and treated with a 50% solution of 1-n-propylphosphonic acid cyclic anhydride in dichloromethane (180 uL, 0.27 mmol, 1.6 eq) followed by the L-methionine benzylamide (71.36 mg, 0.30 mmol, 1.7 eq). Purification by HPLC provided 35 mg (38%) of L-methionine, N-[1-(2-(biphenyl-4-yl)-2-oxoethyl)-L-prolyl] benzylamide.

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-56aba066313d4a7fb2864d09ce843778
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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