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

HRID 2293379Notes

Reaction equation

HRID 2293379 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]([OH:13])=O)=[CH:3][CH:2]=1.C(N1CCOCC1)C.ClCCl.[CH2:35]([NH:42][C:43](=[O:53])[C@H:44]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[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:53])[C@H:44]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[NH2:45])=[O:13])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7525EthylmorpholineHCID 770095Phenylalanine benzylamideHCID 22878946N-[2-(biphenyl-4-yl)-2-oxoethyl] L-proline

Product 1

HCID 67621262L-phenylalanine, N-[1-(2-(biphenyl-4-yl)-2-oxoethyl)-L-prolyl] benzylamideYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-[2-(biphenyl-4-yl)-2-oxoethyl] L-proline (51 mg, 0.16 mmol, 1.0 eq), N-ethylmorpholine (125 uL, 0.98 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 (170 uL, 0.27 mmol, 1.6 eq) followed by phenylalanine benzylamide (49 mg, 0.19 mmol, 3.1 eq). Purification by HPLC provided 12 mg (14%) of L-phenylalanine, N-[1-(2-(biphenyl-4-yl)-2-oxoethyl)-L-prolyl] benzylamide.

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-74be366bbbff412b8a242ab81c7e1162
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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