Triphenylphosphine → HCID 67148390, compound

HRID 2425859Notes

Reaction equation

HRID 2425859 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C@H:35]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36]1.[Cl:47][C:48]1[CH:53]=[CH:52][C:51]([NH:54][S:55]([C:58]2[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[C:60]([O:66][CH3:67])[CH:59]=2)(=[O:57])=[O:56])=[C:50]([CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][N:70]=2)[CH:49]=1>O1CCCC1>[Cl:47][C:48]1[CH:53]=[CH:52][C:51]([N:54]([S:55]([C:58]2[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[C:60]([O:66][CH3:67])[CH:59]=2)(=[O:57])=[O:56])[C@@H:35]2[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36]2)=[C:50]([CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][N:70]=2)[CH:49]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 67148767HCID 67148767, compound

Product 1

HCID 67148390HCID 67148390, compoundYield 162.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.91 ml of diisopropylazodicarboxylate is added at room temperature to 1.21 g of triphenylphosphine in solution in 25 ml of tetrahydrofuran. After 30 minutes, 0.86 g of tert-butyl (3S)-3-hydroxypyrrolidine-1-carboxylate is introduced. After 30 minutes, 1.29 g of N-[4-chloro-2-(pyridin-2-ylmethyl)phenyl]-3,4-dimethoxybenzene-sulfonamide are added and the mixture is left for 18 hours at room temperature. The reaction medium is concentrated and chromatographed on silica gel in order to obtain 2.94 g of the expected product.

Workup

  1. waitAfter 30 minutes
  2. waitthe mixture is left for 18 hours at room temperature
  3. concentrationThe reaction medium is concentrated
  4. customchromatographed on silica gel in order

Sources & evidence

ORD record
ord-3c0d660661794d5faffbfaff2d5d29dd
Source dataset
uspto-grants-2011_06
Patent number
US07968534B2

Reaction notes

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