Triethylamine → HCID 59038207, compound

HRID 1058226Notes

Reaction equation

HRID 1058226 reaction equation
[OH:1][C@@:2]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:24])[C:3]([N:5]1[CH2:23][CH2:22][CH2:21][C@H:6]1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[CH2:18][CH2:19][NH2:20])=[O:8])=[O:4].C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[OH:1][C@@:2]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([CH3:24])[C:3]([N:5]1[CH2:23][CH2:22][CH2:21][C@H:6]1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[CH2:18][CH2:19][NH:20][S:39]([CH3:38])(=[O:41])=[O:40])=[O:8])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59038228HCID 59038228, compound

Product 1

HCID 59038207HCID 59038207, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-((2R)-2-hydroxy-2-phenylpropanoyl)-N-(2-(2-aminoethyl)-5-chlorobenzyl)-L-prolinamide (90 mg, 0.21 mmol) in CH2Cl2 (2 mL) was added triethylamine (50 microliters, 0.35 mmol) and methanesulfonyl chloride (16 microliters, 0.21 mmol). The mixture was stirred at ambient temperature for 30 min. The mixture was diluted with CH2Cl2 (20 mL) and washed with saturated aqueous sodium bicarbonate solution (10 mL). The organic phase was separated, dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give the title compound as an amorphous solid (TLC Rf=0.2 (98:2 CH2Cl2:MeOH); HPLC RT=3.05 min, method A; LC-MS m/z=508).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (10 mL)
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c124f97a72db4d138b3c32ac9e0d7173
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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