1,2-Dichloroethane → HCID 70652350, compound

HRID 1467342Notes

Reaction equation

HRID 1467342 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[C:16](O)=[O:17])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].CC[N:30](C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:30][C:16](=[O:17])[CH:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[F:25]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 70653101HCID 70653101, compound

Product 1

HCID 70652350HCID 70652350, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-((R)-3-(tert-Butoxycarbonylamino)piperidin-1-yl)-2-(2-fluorophenyl)acetic acid (174 mg, 0.494 mmol), ammonium chloride (79 mg, 1.481 mmol), DIPEA (0.431 mL, 2.469 mmol), EDC (142 mg, 0.741 mmol) and HOBT (113 mg, 0.741 mmol) were stirred in DMF (5 mL) at room temperature for 3 days. Saturated NaHCO3 was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification of the residue by MPLC (12-100% EtOAc-hexanes) gave tert-butyl (3R)-1-(2-amino-1-(2-fluorophenyl)-2-oxoethyl)piperidin-3-ylcarbamate as a mixture of diastereoisomers.

Workup

  1. extractionthe products extracted into EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by MPLC (12-100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-86f13a65845143bea5a02eb77b526197
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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