1,2-Dichloroethane → HCID 57888765, compound

HRID 1016168Notes

Reaction equation

HRID 1016168 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH2:16])[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[NH:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@@H:18]([C:22](O)=[O:23])[CH:19]([CH3:21])[CH3:20].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(Cl)CCl>ClCCl>[NH2:16][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:13][CH2:12][N:11]([C:22](=[O:23])[C@H:18]([NH:17][C:25](=[O:26])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:19]([CH3:21])[CH3:20])[CH2:10][C:9]1([CH3:14])[CH3:15]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acidHCID 57888694HCID 57888694, compound

Product 1

HCID 57888765HCID 57888765, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-amine (488 mg, 2.044 mmol), Boc-D-Val-OH (444 mg, 2.044 mmol), HOBT (626 mg, 4.09 mmol), and triethylamine (1.140 mL, 8.18 mmol) in dichloromethane (5 mL) was treated with EDC (784 mg, 4.09 mmol), and the mixture was stirred overnight at room temperature. The mixture was concentrated in-vacuo, and the residue was taken up in ethyl acetate. The organic phase was washed 3× with WATER, 3× with sat. sodium carbonate, and 1× with sat sodium chloride, dried over sodium sulfate, and concentrated in-vacuo. The residue was purified over silica gel, eluting with ethyl acetate/hexanes (25%-50%-100% EtOAc) to yield the title compound (845 mg, 1.929 mmol, 94% yield) as a colorless glass. MS (ESI+)=438.36, M+.

Workup

  1. concentrationThe mixture was concentrated in-vacuo
  2. washThe organic phase was washed 3× with WATER, 3× with sat. sodium carbonate, and 1× with sat sodium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in-vacuo
  5. customThe residue was purified over silica gel
  6. washeluting with ethyl acetate/hexanes (25%-50%-100% EtOAc)

Sources & evidence

ORD record
ord-f23799147c2f4edfa95e55147c157c06
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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