Triacetoxyperiodinane → HCID 10152318, compound

HRID 1180777Notes

Reaction equation

HRID 1180777 reaction equation
[OH:1][CH:2]([C@@H:14]([NH:19][C:20](=[O:35])[O:21][CH2:22][C:23]1([CH2:27][S:28][C:29]2[N:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:26][CH2:25][CH2:24]1)[CH2:15][CH2:16][CH2:17][CH3:18])[C:3](=[O:13])[NH:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[O:13]=[C:3]([NH:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6])[C:2]([C@@H:14]([NH:19][C:20](=[O:35])[O:21][CH2:22][C:23]1([CH2:27][S:28][C:29]2[N:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:24][CH2:25][CH2:26]1)[CH2:15][CH2:16][CH2:17][CH3:18])=[O:1]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 11341008HCID 11341008, compound

Product 1

HCID 10152318HCID 10152318, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.135 g (0.27 mmol) of {1-[(2-pyrimidinylsulfanyl)methyl]cyclobutyl}methyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate in 2.0 mL of dichloromethane was added 0.031 g (0.375 mmol) of sodium bicarbonate followed by the addition of 0.137 g (0.32 mmol) of Dess-Martin periodinane. The reaction was stirred for 15 min and poured directly onto a silica gel column eluting with ethyl acetate:hexane (3:7) as the eluent to afford 0.094 g (70%) of {1-[(2-pyrimidinylsulfanyl)methyl]cyclobutyl}methyl (1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 8.43 (d, J=5 Hz, 2H), 7.31-7.08 (m, 6H), 6.88 (t, J=5 Hz, 1H), 5.25 (d, J=7 Hz, 1H), 4.89-5.20 (m, 2H), 4.08 (s, 2H), 3.43 (s, 2H), 2.03-1.80 (m, 6H), 1.79-1.42 (m, 5H), 1.41-1.25 (m, 4H), 0.81 (br s, 3H). LC-MS m/z 499 (M+H).

Workup

  1. additionpoured directly onto a silica gel column
  2. washeluting with ethyl acetate:hexane (3:7) as the eluent

Sources & evidence

ORD record
ord-658d59771cc24ab2a3b5bf83eca27065
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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