Triphenylphosphine → HCID 59093854, compound

HRID 324600Notes

Reaction equation

HRID 324600 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[NH:3]1.[CH3:20][O:21][C:22](=[O:46])[C@H:23]([CH2:44]O)[NH:24][C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:20][O:21][C:22]([C@@H:23]([NH:24][C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:44][N:6]1[C:5](=[O:7])[C:4]2([CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[NH:3][C:2]1=[O:1])=[O:46]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3629994Tert-butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylateHCID 7128367N-(Triphenylmethyl)-L-serine methyl ester

Product 1

HCID 59093854HCID 59093854, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.6 g (13.37 mmol) of (34.2) in 15 ml of absolute THF is added to a solution of 3.72 g (10.3 mmol) of (34.3) and 3.5 g (13.34 mmol) of triphenylphosphine in 20 ml of absolute THF. 2.11 ml (13.37 mmol) of diethyl azodicarboxylate (DEAD) are added to this solution and the reaction mixture is stirred at room temperature until the reaction has come to an end. The solvent is removed in vacuo and the residue is chromatographed through silica gel using heptane/ethyl acetate. 6 g (95%) of (34.4) are obtained after concentrating the product fractions.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is chromatographed through silica gel

Sources & evidence

ORD record
ord-c3af4a3315e245ab93395b93a5e5a82d
Source dataset
uspto-grants-2001_04
Patent number
US06218415B1

Reaction notes

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