Triacetoxyperiodinane → HCID 20639928, compound

HRID 635634Notes

Reaction equation

HRID 635634 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]([NH:12][C@H:13]([C:22]([NH:24][C@H:25]([C:35]([NH:37][C@H:38]([C:47]([NH:49][C@H:50]([C:55]([NH:57][C@H:58]([C:63]([NH:65][CH:66]([CH2:72][C:73]([F:76])([F:75])[F:74])[CH:67]([OH:71])[C:68]([NH2:70])=[O:69])=[O:64])[CH2:59][CH:60]([CH3:62])[CH3:61])=[O:56])[C:51]([CH3:54])([CH3:53])[CH3:52])=[O:48])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH3:46])=[O:36])[CH2:26][CH2:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:23])[CH2:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl>[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]([NH:12][C@H:13]([C:22]([NH:24][C@H:25]([C:35]([NH:37][C@H:38]([C:47]([NH:49][C@H:50]([C:55]([NH:57][C@H:58]([C:63]([NH:65][CH:66]([CH2:72][C:73]([F:74])([F:75])[F:76])[C:67](=[O:71])[C:68]([NH2:70])=[O:69])=[O:64])[CH2:59][CH:60]([CH3:62])[CH3:61])=[O:56])[C:51]([CH3:52])([CH3:53])[CH3:54])=[O:48])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH3:46])=[O:36])[CH2:26][CH2:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:23])[CH2:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 20639929HCID 20639929, compound

Product 1

HCID 20639928HCID 20639928, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.7 g (0.645 mmol) of 3(RS)-[[N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)-propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]-5,5,5-trifluoro-2(RS)-hydroxyvaleramide and 328 mg (0.773 mmol) of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one in 20 ml of dichloromethane was stirred under a nitrogen atmosphere at room temperature for 30 minutes. A further 328 mg. (0.773 mmol) of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one were added and the mixture was stirred for 1 hour. The solution was extracted with a solution of 10 g of sodium thiosulphate in 40 ml of saturated sodium bicarbonate solution then dried over anhydrous magnesium sulphate, filtered and evaporated to dryness. The residue was triturated with diethyl ether/petroleum ether (1:1) and the solid was removed by filtration to give 660 mg of 3(RS)-[[N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]-5,5,5-trifluoro-2-oxovaleramide as a white solid. MS: m/e 1084.5 [M+H]+.

Workup

  1. extractionThe solution was extracted with a solution of 10 g of sodium thiosulphate in 40 ml of saturated sodium bicarbonate solution
  2. dry with materialthen dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was triturated with diethyl ether/petroleum ether (1:1)
  6. customthe solid was removed by filtration

Sources & evidence

ORD record
ord-dc0110f79c934fd69e9e7d859f5ecd3a
Source dataset
uspto-grants-2001_02
Patent number
US06187905B1

Reaction notes

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