Triethylamine → HCID 54408318, compound

HRID 1017995Notes

Reaction equation

HRID 1017995 reaction equation
[C:1]([O:5][C:6](=[O:39])[CH2:7][C@@H:8]([NH2:38])[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:37])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[O:26])=[C:20]([O:35][CH3:36])[CH:19]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:47][S:48](Cl)(=[O:50])=[O:49]>ClCCl>[C:1]([O:5][C:6](=[O:39])[CH2:7][C@H:8]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:37])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[O:26])=[C:20]([O:35][CH3:36])[CH:19]=2)=[CH:13][CH:14]=1)[NH:38][S:48]([CH3:47])(=[O:50])=[O:49])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53940187HCID 53940187, compound

Product 1

HCID 54408318HCID 54408318, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (R)-3-amino-3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetylamino}-phenyl)-propanoic acid tert-butyl ester [100 mg, Reference Example 7(a)], dichloromethane (10 ml) and triethylamine (38 mg) was stirred at ambient temperature and then treated with methanesulphonyl chloride (22 mg). After stirring for 1 hour, the reaction mixture was diluted with dichloromethane (20 ml) and then washed with hydrochloric acid (20 ml, 1M), then with saturated aqueous sodium bicarbonate solution (20 ml). The organic layer was dried over magnesium sulphate and then evaporated to give the title compound (55 mg) as a white solid.

Workup

  1. stirringAfter stirring for 1 hour
  2. washwashed with hydrochloric acid (20 ml, 1M)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-450fff3e337f49898473f353e5f6bdc5
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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