Triphenylphosphine → HCID 7019602, compound

HRID 849702Notes

Reaction equation

HRID 849702 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:34]([C@@H:41]([CH2:45]O)[C:42]([OH:44])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:47]([OH:50])(=[S:49])[CH3:48]>O1CCCC1>[C:47]([S:49][CH2:45][C@H:41]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:42]([OH:44])=[O:43])(=[O:50])[CH3:48]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 444512HCID 444512, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 7019602HCID 7019602, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

2.44 g (12.05 mmol) of diisopropyl azodicarboxylate are added dropwise, at 0° C., to a solution of 3.16 g (12.05 mmol) of triphenylphosphine in 30 ml of tetrahydrofuran. Once the addition is complete, the mixture is stirred for 30 minutes at this temperature. The reaction medium is cooled to -10° C. and a solution of 1.45 g (8.05 mmol) of (S)-2-benzyl-3-hydroxypropionic acid (X S) and 0.92 g (12.05 mmol) of thioacetic acid in 10 ml of tetrahydrofuran is added dropwise. Once the addition is complete, the mixture is stirred for one hour at -10° C. and for a further two hours at room temperature.

Workup

  1. additionOnce the addition
  2. additionOnce the addition
  3. stirringthe mixture is stirred for one hour at -10° C. and for a further two hours at room temperature

Sources & evidence

ORD record
ord-d607698ee9ed41d6b68fc2bcb96a3776
Source dataset
uspto-grants-2000_01
Patent number
US06013829

Reaction notes

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