1,2-Dichloroethane → HCID 69155362, compound

HRID 854285Notes

Reaction equation

HRID 854285 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=1[F:23])[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH3:38][C@H:39]1[NH:45][CH2:44][C@@H:43]([CH3:46])[CH2:42][NH:41][C:40]1=[O:47]>C(#N)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=1[F:23])[CH2:10][C:11]([N:45]1[CH2:44][C@@H:43]([CH3:46])[CH2:42][NH:41][C:40](=[O:47])[C@H:39]1[CH3:38])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7146288(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid2×HCID 55300255HCID 55300255, compound2×

Product 1

HCID 69155362HCID 69155362, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (Intermediate 3, 120 mg, 0.36 mmol) in acetonitrile (10 mL) was added HOBT (60 mg, 0.43 mmol) and EDC (75 mg, 0.4 mmol). The reaction was stirred at room temperature for 1 h and then treated with (3R,6R)-hexahydro-3,6-dimethyl-2H-1,4-diazepin-2-one (Intermediate 23, 50 mg, 0.35 mmol). The reaction was stirred at room temperature overnight. After removal of solvent, the crude product was purified by flash chromatography on a Biotage® system (silica, 6% methanol in dichloromethane) to yield the title compound as white solid. MS (M+1−Boc): 358.0

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. customAfter removal of solvent
  3. customthe crude product was purified by flash chromatography on a Biotage® system (silica, 6% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1fa4d2a7f06f420d8bde43a918163156
Source dataset
uspto-grants-2007_08
Patent number
US07259160B2

Reaction notes

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