Triphenylphosphine → Benzyl-{2-[4-(4-phenyl-thiazol-2-yl)-phenoxy]-ethyl}-carbamate

HRID 49376

Reaction equation

HRID 49376 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:39][CH2:40][NH:41][C:42](=[O:51])[O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1(C)C=CC=CC=1.O1CCCC1>[CH2:44]([O:43][C:42](=[O:51])[NH:41][CH2:40][CH2:39][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[S:10][CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)=[CH:17][CH:16]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 280458benzyl N-(2-hydroxyethyl)carbamateHCID 1356483144-(4-Phenyl-1,3-thiazol-2-yl)phenol

Product 1

HCID 12071998Benzyl-{2-[4-(4-phenyl-thiazol-2-yl)-phenoxy]-ethyl}-carbamateYield 45.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(4-Phenyl-thiazol-2-yl)-phenol (516 mg, 2.03 mmol) was dissolved in toluene (6.8 ml), and triphenylphosphine (786 mg, 3.00 mmol) and benzyl N-(2-hydroxyethyl)-carbamate (585 mg, 3.00 mmol) were added. The solution was cooled to about 0° C. and 1,1-(azodicarbonyl)-dipiperidine (757 mg, 3.00 mmol) was added. The mixture was allowed to stir for about 10 minutes at about 0° C. and was then allowed to warm to room temperature. An additional 6.8 ml of toluene and 6.8 ml of tetrahydrofuran were added to the viscous solution. The reaction mixture was stirred for about forty-eight hours, and then the solids were filtered off and rinsed with a minimum volume of 1:1 toluene/tetrahydrofuran. The filtrate was concentrated in vacuo to a semisolid which was then purified by column chromatography (silica gel; methylene chloride to 2% methanol/methylene chloride) to give 396 mg of pure product (45% yield). LRMS ([M+H]+)=430.9.

Workup

  1. temperatureto warm to room temperature
  2. stirringThe reaction mixture was stirred for about forty-eight hours
  3. filtrationthe solids were filtered off
  4. washrinsed with a minimum volume of 1:1 toluene/tetrahydrofuran
  5. concentrationThe filtrate was concentrated in vacuo to a semisolid which
  6. customwas then purified by column chromatography (silica gel; methylene chloride to 2% methanol/methylene chloride)

Sources & evidence

ORD record
ord-5fa7e2edfe1d42a091f266ad74be7784
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Linked notes

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