Triethylamine → HCID 86594557, compound

HRID 1744091Notes

Reaction equation

HRID 1744091 reaction equation
[C:1]1([N:7]2[C:11]([NH:12][C@H:13]([C:18]([OH:20])=O)[CH2:14][CH:15]([CH3:17])[CH3:16])=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:22][CH2:23][C:24]#[N:25].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[C:23]([CH2:24][NH:25][C:18](=[O:20])[C@H:13]([CH2:14][CH:15]([CH3:16])[CH3:17])[NH:12][C:11]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[N:9][N:10]=1)#[N:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 69152081HCID 69152081, compound

Product 1

HCID 86594557HCID 86594557, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(1-phenyl-1H-tetraazol-5-yl)-L-leucine (100 mg, 0.36 mmol), aminoacetonitrile hydrochloride (62 mg, 0.68 mmol) and PyBOP (230 mg, 0.44 mmol) in DMF (3 mL) was added triethylamine (0.2 mL, 1.4 mmol). The solution was stirred 36 h, then partitioned between ethyl acetate and pH 3 phosphate buffer. The organic phase was washed with brine and concentrated. Purification by flash chromatography (60% to 90% ethyl acetate/hexanes) gave 62 mg of N1-(cyanomethyl)-N2-(1-phenyl-1H-tetraazol-5-yl)-L-leucinamide. MS (+APCI): 313.9 [M+1]+.

Workup

  1. custompartitioned between ethyl acetate and pH 3 phosphate buffer
  2. washThe organic phase was washed with brine
  3. concentrationconcentrated
  4. customPurification by flash chromatography (60% to 90% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cc03df82f4c5412db659575f1b09058c
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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