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Sodium Thiosulfate → HCID 44819177, compound

HRID 1158510
Notes
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Reaction equation

HRID 1158510 reaction equation
[CH2:1]([C@:8]([OH:28])([CH2:25][CH2:26][OH:27])[C:9]([N:11]1[C@H:15]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[CH2:22][C@H:14]2[O:13][C:12]1([CH3:24])[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.CCOCC>[CH2:1]([C@@:8]([OH:28])([C:9]([N:11]1[C@H:15]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[CH2:22][C@H:14]2[O:13][C:12]1([CH3:23])[CH3:24])=[O:10])[CH2:25][CH:26]=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 44818263HCID 44818263, compound

Product 1

HCID 44819177HCID 44819177, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-2-benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3 aH-indeno[1,2-d]oxazol-3-yl)-2,4-dihydroxy-butan-1-one (21g) (0.13 g, 0.34 mmol) in dry CH2Cl2 (5 mL) was added over 1 min to a stirred solution of Dess-Martin periodinate (0.16 g, 0.37 mmol) in dry CH2Cl2 (10 mL). After 30 min the homogeneous mixture was diluted with ether and poured into cold saturated NaHCO3 (10 mL) containing Na2S2O3 (2.2 g). Organic layers were washed with aqueous saturated NaHCO3, brine and dried (MgSO4). The solvents were evaporated below 20° C. to give the title compound (0.082 g, 64%). The residue [MS (ESI+): 380 (M++1)] was immediately used for the next step.

Workup

  1. washOrganic layers were washed with aqueous saturated NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. customThe solvents were evaporated below 20° C.

Sources & evidence

ORD record
ord-12cb03bfe2b94ab6a2b40cae4c397205
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07807677B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes