Dichloromethane → L-isoleucine, N-[1-(2-(biphenyl-4-yl)-2-oxoethyl)-L-prolyl] tert-butylamide

HRID 2293378Notes

Reaction equation

HRID 2293378 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.[C:35]([NH:39][C:40](=[O:47])[C@H:41]([C@H:43]([CH2:45][CH3:46])[CH3:44])[NH2:42])([CH3:38])([CH3:37])[CH3:36]>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:39]([C:35]([CH3:37])([CH3:36])[CH3:38])[C:40](=[O:47])[C@H:41]([C@H:43]([CH2:45][CH3:46])[CH3:44])[NH2:42])=[O:12])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7525EthylmorpholineHCID 22878946N-[2-(biphenyl-4-yl)-2-oxoethyl] L-prolineHCID 42314162L-isoleucine tert-butylamide

Product 1

HCID 131720278L-isoleucine, N-[1-(2-(biphenyl-4-yl)-2-oxoethyl)-L-prolyl] tert-butylamideYield 16%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-[2-(biphenyl-4-yl)-2-oxoethyl] L-proline (50 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 L-isoleucine tert-butylamide (49 mg, 0.19 mmol, 1.1 eq). Purification by HPLC provided 12 mg (16%) of L-isoleucine, N-[1-(2-(biphenyl-4-yl)-2-oxoethyl)-L-prolyl] tert-butylamide.

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-db2829083ee5431dbdc3ba2858bfefbe
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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