Ammonium Chloride → HCID 87549033, compound

HRID 657692Notes

Reaction equation

HRID 657692 reaction equation
[OH:1][C:2]([CH:6]1[CH2:9][CH:8]([CH2:10][C:11](O)=[O:12])[C:7]1([CH3:15])[CH3:14])([C:4]#[CH:5])[CH3:3].[Cl-].[NH4+].F[B-](F)(F)F.[N:23]1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[OH:1][C:2]([CH:6]1[CH2:9][CH:8]([CH2:10][C:11]([NH2:23])=[O:12])[C:7]1([CH3:15])[CH3:14])([C:4]#[CH:5])[CH3:3]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 262808[3-(2-hydroxybut-3-yn-2-yl)-2,2-dimethylcyclobutyl]acetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 87549033HCID 87549033, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of Example 29A (84 mg, 0.4 mmol), ammonium chloride (32 mg, 0.6 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (154 mg, 0.48 mmol) in N,N-dimethylformamide was added N,N-diisopropylethylamine (348 μL, 2.0 mmol). The reaction mixture was stirred at room temperature overnight. It was partitioned between ethyl acetate and saturated NaHCO3. The organic phase was washed with brine twice, dried (MgSO4), filtered and concentrated in vacuo to provide the title intermediate as a white solid (50 mg, 60% yield).

Workup

  1. customIt was partitioned between ethyl acetate and saturated NaHCO3
  2. washThe organic phase was washed with brine twice
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d446d4a0020148b7a15f1c8d18932a79
Source dataset
uspto-grants-2011_12
Patent number
US08076344B2

Reaction notes

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