1,2-Dichloroethane → HCID 69838708, compound

HRID 352711Notes

Reaction equation

HRID 352711 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH3:38])[O:9][N:8]=[C:7]([C@@H:10]([NH:20][C:21]([O:23]CC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6]1)=[O:4].N1CCCCC1.[CH:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47][C:46]=1C(O)=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1([CH3:38])[O:9][N:8]=[C:7]([C@@H:10]([NH:20][C:21]([C:47]2[CH:46]=[CH:45][C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[CH:48]=2)=[O:23])[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:6]1)=[O:4]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 71232-Naphthoic acidHCID 8082PiperidineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 69838250HCID 69838250, compound

Product 1

HCID 69838708HCID 69838708, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[(1S)-1-(9-fluorenylmethyloxycarbonylamino)-3-t-butoxycarbonyl-propyl]-5-methyl-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester (440 mg, 0.842 mmol) in DMF (8.0 mL) at room temperature was treated with piperidine (2.5 mL) for 5 min. After concentration, the residue was dissolved in DMF (10 mL), and treated with 2-naphthoic acid (174 mg, 1.2 eq), EDC (210 mg, 1.3 eq), HOBt (148 mg, 1.3 eq) and triethylamine (0.35 mL, 3.0 eq), then sired overnight (0° C. to room temperature). Usual workup followed by chromatography gave 133 mg of the title compound and 260 mg (˜50% purity) mixture.

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in DMF (10 mL)
  3. customsired overnight (0° C. to room temperature)

Sources & evidence

ORD record
ord-8535ac1de1ea45b2832397ed5d5bd799
Source dataset
uspto-grants-2004_06
Patent number
US06747050B1

Reaction notes

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