Triacetoxyperiodinane → HCID 23648431, compound

HRID 1182289Notes

Reaction equation

HRID 1182289 reaction equation
[OH:1][C@H:2]([C@@H:14]([NH:19][C:20](=[O:43])[O:21][C@H:22]([CH2:27][N:28]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[N:29]1)[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:7])=[O:6].O[C@@H]([C@@H](NC(=O)O[C@H](CN1C=CC(C2C=CC(C(F)(F)F)=CC=2)=N1)C(C)(C)C)CCCC)CNS(C1C=CC=CN=1)(=O)=O.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[S:5]([NH:4][CH2:3][C:2]([C@@H:14]([NH:19][C:20](=[O:43])[O:21][C@H:22]([CH2:27][N:28]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:40])[F:41])=[CH:35][CH:34]=2)=[N:29]1)[C:23]([CH3:25])([CH3:26])[CH3:24])[CH2:15][CH2:16][CH2:17][CH3:18])=[O:1])(=[O:6])=[O:7]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 71164616HCID 71164616, compoundHCID 71164617HCID 71164617, compound

Product 1

HCID 23648431HCID 23648431, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 90 mg (0.14 mmol) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate in 2 mL of dichloromethane was added 76 mg (0.18 mmol) of Dess-Martin periodinane. The reaction mixture was stirred for 15 min, and then filtered through a celite plug with dichloromethane. The filtrate was concentrated, and the residue was purified by silica gel chromatography eluting with ethyl acetate:hexanes (6.5:3.5) to afford 56 mg (62%) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{[(2-pyridinylsulfonyl)amino]acetyl}pentylcarbamate. 1H-NMR (300 MHz, T=100° C., DMSO6): δ 8.66 (d, J=4 Hz, 1H), 8.08–7.60 (m, 9H), 7.17 (m, 1H), 6.72 (d, J=2 Hz, 1H), 4.90 (d, J=9 Hz, 1H), 4.49 (d, J=14 Hz, 1H), 4.26–3.85 (m, 4H), 1.56 (m, 1H), 1.40 (m, 1H), 1.29–1.01 (m, 13H) 0.78 (m, 3H); ES-LCMS m/z 646 (M+Na); HRMS C29H36F3N5O5S1 m/z 646.2287 (M+Na)+Cal; 646.2283 (M+Na)+.

Workup

  1. filtrationfiltered through a celite plug with dichloromethane
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with ethyl acetate:hexanes (6.5:3.5)

Sources & evidence

ORD record
ord-56ea842b7fed4c8a8608ae28ef056c02
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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