Pyridine → HCID 58717638, compound

HRID 1784247Notes

Reaction equation

HRID 1784247 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([NH:25][C:26](=[O:35])[C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[NH2:34])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:8][CH:7]=1.N1C=CC=CC=1.[CH3:43][N:44]([CH3:59])[C:45]1[CH:54]=[CH:53][CH:52]=[C:51]2[C:46]=1[CH:47]=[CH:48][CH:49]=[C:50]2[S:55](Cl)(=[O:57])=[O:56]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([NH:25][C:26](=[O:35])[C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[NH:34][S:55]([C:50]1[C:51]2[C:46](=[C:45]([N:44]([CH3:59])[CH3:43])[CH:54]=[CH:53][CH:52]=2)[CH:47]=[CH:48][CH:49]=1)(=[O:57])=[O:56])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11801Dansyl chlorideHCID 68859581HCID 68859581, compound

Product 1

HCID 58717638HCID 58717638, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (S)-2(2-amino-5-chloro-benzoylamino)-3-(2′-phenoxy-biphenyl-4-yl)propionic acid methyl ester (100 mg, 0.2 mmol) prepared above dissolved in DCM containing pyridine (31.6 mg, 0.4 mmol), was added 5-Dimethylamino-naphthalene-1-sulfonyl chloride (59.1 mg, 0.0.22 mmol) at 0° C. The reaction mixture was stirred at rt for 3 h, extracted with DCM, washed with 1M HCl and brine evaporation followed by column chromatography purification (silica, CH2Cl2) giving (2S)-[5-chloro-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-benzoylamino]-3-(2′-phenoxy-biphenyl-4-yl)-propionic acid methyl ester (100 mg) as a light yellow solid which was hydrolyzed according to Procedure C yielding the title compound (93 mg) as a light yellow solid. LC/MS (m/z): 720 (M+1)+.

Workup

  1. extractionextracted with DCM
  2. washwashed with 1M HCl and brine evaporation
  3. customfollowed by column chromatography purification (silica, CH2Cl2)

Sources & evidence

ORD record
ord-b130170f2b6845db8a0421cbc4f1be3d
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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