Tributylphosphine → HCID 18625932, compound

HRID 1860087Notes

Reaction equation

HRID 1860087 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19](O)[C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[SH:25][C:26]1[O:27][C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>>[O:27]1[C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=[C:26]1[S:25][CH:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:13][CH:14]=1)[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 18625783HCID 18625783, compoundHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 18625932HCID 18625932, compoundYield 115.1%

Procedure

In a similar manner to that described in Example 122, a reaction was carried out using methyl 3-[4-(2-t-butoxycarbonylaminoethoxy)phenyl]-2-hydroxypropionate (415 mg), which is obtained in a similar manner to that described in Reference example 39(a), 2-mercaptobenzoxazole (277 mg), tributylphosphine (0.46 ml) instead of triphenylphosphine and 1,1′-(azodicarbonyl)dipiperidine (460 mg) instead of diethylazodicarboxylate and the reaction mixture was treated to afford the desired compound (665 mg) as a colorless oil which contained some impurities.

Workup

  1. customwhich is obtained in a similar manner to that
  2. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-b6e1a6cdb23b40b184a14c8df663cb97
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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