Ammonium Chloride → cis-[3-(3-Diphenylcarbamoyloxypropenyl)phenoxy]acetic acid tert-butyl ester

HRID 1250113Notes

Reaction equation

HRID 1250113 reaction equation
C([N-]C(C)C)(C)C.[Li+].O1CCCC1.CCCCCCC.C(C1C=CC=CC=1)C.[C:29]([O:33][C:34](=[O:47])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39](/[CH:43]=[CH:44]\[CH2:45][OH:46])[CH:38]=1)([CH3:32])([CH3:31])[CH3:30].[C:48]1([N:54]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:55](Cl)=[O:56])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.[Cl-].[NH4+]>O1CCCC1>[C:29]([O:33][C:34](=[O:47])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39](/[CH:43]=[CH:44]\[CH2:45][O:46][C:55](=[O:56])[N:54]([C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:38]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 65741N,N-Diphenylcarbamic chlorideHCID 2724682Lithium diisopropylamideHCID 22742125Tetrahydrofuran heptane ethylbenzolHCID 69992070cis-[3-(3-Hydroxypropenyl)phenoxy]acetic acid tert-butyl ester

Product 1

HCID 69990470cis-[3-(3-Diphenylcarbamoyloxypropenyl)phenoxy]acetic acid tert-butyl esterYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 M Lithium diisopropylamide in a solution of tetrahydrofuran/heptane/ethylbenzene (0.9 mL, 1.8 mmol) was added to a stirred solution of cis-[3-(3-hydroxypropenyl)phenoxy]acetic acid tert-butyl ester (421 mg, 1.56 mmol) in tetrahydrofuran (4.5 mL) at −78° C. under an argon atmosphere. The mixture was stirred for 10 minutes and solid diphenylcarbamoyl chloride (361 mg, 1.56 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 dried over sodium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate (9:1), gave cis-[3-(3-diphenylcarbamoyloxypropenyl)phenoxy]acetic acid tert-butyl ester (433 mg, 60.4%).

Workup

  1. customto reach 0-5° C.
  2. stirringstirred for 16 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification by flash chromatography
  7. washeluting with hexane/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-79c46d5d51a14467baeaebd13d3a2553
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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