Triphenylphosphine → HCID 67080710, compound

HRID 655519Notes

Reaction equation

HRID 655519 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.[C:34]([O:38][C:39](=[O:64])[N:40]([CH2:51][CH2:52][C:53](=[O:63])[NH:54][O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C@@H:41]([CH2:49]O)[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([CH3:37])([CH3:36])[CH3:35]>O1CCCC1>[C:34]([O:38][C:39]([N:40]1[CH2:51][CH2:52][C:53](=[O:63])[N:54]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH2:49][C@H:41]1[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:64])([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86638108HCID 86638108, compound

Product 1

HCID 67080710HCID 67080710, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropyl azodicarboxylate (806 mg, 3.75 mmol) was added at <10° C. to a solution of triphenylphosphine (983 mg, 3.75 mmol) in tetrahydrofuran (60 ml), followed by addition of a solution of (2-benzyloxycarbamoyl-ethyl)-((R)-1-hydroxymethyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (1.24 g, 2.88 mmol) in tetrahydrofuran (12 ml). The reaction mixture was stirred at <10° C. for 16 h, then concentrated. The residue was purified by chromatography (SiO2; heptane/ethyl acetate 7:3) to afford the title compound (800 mg, 68%). Light yellow oil, MS (ISP)=411.3 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography (SiO2; heptane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-4b08c60d3ee4448aaba1cc27ec2c58a7
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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