Tetrahydrofuran → HCID 53896352, compound

HRID 1018008Notes

Reaction equation

HRID 1018008 reaction equation
[CH3:1][O:2][C:3](=[O:36])[CH2:4][C@@H:5]([NH2:35])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:34])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])=[O:23])=[C:17]([O:32][CH3:33])[CH:16]=2)=[CH:8][CH:7]=1.O1CCCC1.[S:42](Cl)([C:45]1[C:57]2[CH:56]=[CH:55][CH:54]=[C:50]([N:51]([CH3:53])[CH3:52])[C:49]=2[CH:48]=[CH:47][CH:46]=1)(=[O:44])=[O:43]>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:36])[CH2:4][C@@H:5]([NH:35][S:42]([C:45]1[C:57]2[C:49](=[C:50]([N:51]([CH3:53])[CH3:52])[CH:54]=[CH:55][CH:56]=2)[CH:48]=[CH:47][CH:46]=1)(=[O:44])=[O:43])[C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:34])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])=[O:23])=[C:17]([O:32][CH3:33])[CH:16]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11801Dansyl chlorideHCID 54354360HCID 54354360, compound

Product 1

HCID 53896352HCID 53896352, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of (R)-3-amino-3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetylamino}-phenyl)-propanoic acid methyl ester (0.75 g, Reference Example 30), anhydrous tetrahydrofuran (25 ml), dansyl chloride (0.62 g) and triethylamine (1.0 ml) was placed under an atmosphere of argon and stirred at ambient temperature for 4 hours then heated to reflux for 2 hours. The reaction mixture was cooled then filtered. The filtrate was evaporated and the residue was subjected to flash chromatography on silica gel eluting with a mixture of dichloromethane and methanol (49: 1, v/v to give the title compound (0.89 g) as a yellow solid.

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationthen filtered
  5. customThe filtrate was evaporated
  6. additionthe residue was subjected to flash chromatography on silica gel eluting with a mixture of dichloromethane and methanol (49: 1, v/v

Sources & evidence

ORD record
ord-6396235297e243429a92e82001f68472
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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