Dichloromethane → L-Isoleucine

HRID 2293377Notes

Reaction equation

HRID 2293377 reaction equation
C1(C2C=CC=CC=2)C=CC(C(=O)CN2CCC[C@H]2C(O)=O)=CC=1.C(N1CCOCC1)C.ClCCl.C1(C(N)=O)C2C(=CC=CC=2)CCN1.[NH2:48][C@H:49]([C:54]([OH:56])=[O:55])[C@H:50]([CH2:52][CH3:53])[CH3:51]>C(#N)C>[NH2:48][C@H:49]([C:54]([OH:56])=[O:55])[C@H:50]([CH2:52][CH3:53])[CH3:51]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7525EthylmorpholineHCID 22878869L-isoleucine 1,2,3,4-tetrahydroisoquinolinamideHCID 22878946N-[2-(biphenyl-4-yl)-2-oxoethyl] L-proline

Product 1

HCID 6306L-IsoleucineYield 22.2%

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, 0.97 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, 0.26 mmol, 1.6 eq) followed by the L-isoleucine 1,2,3,4-tetrahydroisoquinolinamide (47.9 mg, 0.19 mmol, 1.2 eq). Purification by HPLC provided 5.53 mg (6.3%) of L-Isoleucine, N-[1-(2-(Biphenyl-4-yl)-2-oxoethyl)-L-prolyl]1,2,3,4-tetrahydroisoquinolinamide.

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-ac8608ae64f14d49bbdb55fa33b92d0b
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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