1,2-Dichloroethane → HCID 67386425, compound

HRID 245798Notes

Reaction equation

HRID 245798 reaction equation
[C:1]([NH:8][C@@H:9]([C:14]([OH:16])=O)[C:10]([CH3:13])([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH:31]1[CH2:36][CH2:35][CH:34]([C:37]#[N:38])[CH2:33][CH2:32]1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:4]([O:3][C:1](=[O:2])[NH:8][C@@H:9]([C:14]([N:31]1[CH2:36][CH2:35][CH:34]([C:37]#[N:38])[CH2:33][CH2:32]1)=[O:16])[C:10]([CH3:11])([CH3:12])[CH3:13])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1382234-CyanopiperidineHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid

Product 1

HCID 67386425HCID 67386425, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A round-bottomed flask was charged with Boc-D-tert-leucine (2.5 g, 10.8 mmol), HOBT (4.2 g, 24.9 mmol), EDC (4.77 g, 24.9 mmol) and piperidine-4-carbonitrile (2.98 g, 27.0 mmol). Then added DMF (50 mL) followed by N,N-diisopropylethylamine (10.7 ml, 61.6 mmol). The yellow reaction mixture was stirred at room temperature overnight then quenched with 10% citric acid and extracted with EtOAc (2×). The combined organic layers were washed twice with 10% citric acid, twice with sat'd LiCl and once with brine then dried over MgSO4, filtered and concentrated to give 3.4 g (97%) of [(R)-1-(4-cyano-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-carbamic acid tert-butyl ester as a beige foamy solid.

Workup

  1. customthen quenched with 10% citric acid
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed twice with 10% citric acid, twice with sat'd LiCl and once with brine
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b25b487430594d9a8a8741478036f9a0
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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