Sodium Thiosulfate → HCID 86585180, compound

HRID 392029Notes

Reaction equation

HRID 392029 reaction equation
[C:1]([O:5][C:6](=[O:38])[CH2:7][CH:8]([NH:13][C:14]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][N:17]1[C:22]([N:24]1[C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[S:31][C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:23])=[O:15])[CH:9]([OH:12])[CH2:10][F:11])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:38])[CH2:7][CH:8]([NH:13][C:14]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][N:17]1[C:22]([N:24]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=2[S:31][C:32]2[C:37]1=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:23])=[O:15])[C:9](=[O:12])[CH2:10][F:11])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67058728HCID 67058728, compound

Product 1

HCID 86585180HCID 86585180, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of [3S/R, 4S/R (2S)]-5-fluoro-4-hydroxy-3-{[1-(phenothiazine-10-carbonyl)piperidine-2-carbonyl]amino}-pentanoic acid tertbutyl ester (294 mg, 0.541 mmol) in anhydrous DCM (10 mL) was treated with 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (344 mg, 0.812 mmol) at 0° C. The resulting mixture was allowed to warm to room temperature over 2 h, diluted with ethyl acetate, then poured into a 1:1 mixture of saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium thiosulphate. The organic layer was removed and the aqueous layer re-extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (30% ethyl acetate in hexane) to afford the sub-title compound as a pale pink foam (220 mg, 75%): 1H NMR (400 MHz, CDCl3) δ 0.84-0.96 (1H, m), 1.20-1.40 (10H, m+2s), 1.51-1.56 (3H, m), 2.20-2.27 (1H, m), 2.70-2.98 (3H, m), 3.49-3.63 (1H, m), 4.74-5.24 (4H, m), 7.14-7.18 (2H, m), 7.28-7.38 (4H, m), 7.48-7.79 (3H, m); 13C (100 MHz, CDCl3) δ 20.8/21.0 (CH2), 23.7/23.9 (CH2), 25.8/25.9 (CH2), 28.2/28.3 (CH3), 36.8/36.9 (CH2), 46.0/46.1 (CH2), 52.9 (CH), 56.8 (CH), 82.6 (C), 84.4/84.5 (2d, J 184.0/183.3, CH2F), 123.7/123.8 (CH), 126.1 (CH), 128.0/128.1 (CH), 128.2/128.3 (CH), 130.4/130.5 (C), 141.4 (C), 160.0 (C), 170.0 (C), 171.7 (C), 202.9 (C); 19F (376 MHz, CDCl3) δ -231.9 (t), −232.2 (t).

Workup

  1. customThe organic layer was removed
  2. extractionthe aqueous layer re-extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2a28120d1ab442cfac26a2616d34454c
Source dataset
uspto-grants-2004_10
Patent number
US06800619B2

Reaction notes

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