Ammonium Chloride → HCID 53995625, compound

HRID 1250109Notes

Reaction equation

HRID 1250109 reaction equation
C([N-]C(C)C)(C)C.[Li+].C1(C)C=CC=CC=1.CCCCCCC.C(C1C=CC=CC=1)C.[C:31]([O:35][C:36](=[O:50])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([C:45]#[C:46][CH2:47][OH:48])[C:40]=1[CH3:49])([CH3:34])([CH3:33])[CH3:32].[C:51]1([N:57]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:58](Cl)=[O:59])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.[Cl-].[NH4+]>O1CCCC1>[C:31]([O:35][C:36](=[O:50])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([C:45]#[C:46][CH2:47][O:48][C:58](=[O:59])[N:57]([C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:40]=1[CH3:49])([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 65741N,N-Diphenylcarbamic chlorideHCID 2724682Lithium diisopropylamideHCID 53810356HCID 53810356, compoundHCID 86757709HCID 86757709, compound

Product 1

HCID 53995625HCID 53995625, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 M Lithium diisopropylamide in toluene/heptane/ethylbenzene (0.77 mL, 1.54 mmol) was added to a stirred solution of [3-(3-hydroxyprop-1-ynyl)-2-methylphenoxy]acetic acid tert-butyl ester (370 mg, 1.34 mmol) in tetrahydrofuran (4 mL) at −78° C. under an argon atmosphere. The mixture was stirred for 10 minutes and solid diphenylcarbamyl chloride (310 mg, 1.34 mmol) was added. The mixture was allowed to reach 0-5° C. and stirred for 16 hours. Saturated ammonium chloride was added and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate, gave [3-(3-diphenylcarbamoyloxyprop-1-ynyl)-2-methylphenoxy]acetic acid tert-butyl ester as a colorless oil (220 mg, 35%).

Workup

  1. customto reach 0-5° C.
  2. stirringstirred for 16 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness
  7. customPurification by flash chromatography
  8. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-fda3646c07514814a9a44c6a47a7b98e
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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