Sodium Thiosulfate → HCID 25124718, compound

HRID 2038559Notes

Reaction equation

HRID 2038559 reaction equation
[CH:1]1([CH2:7][C:8]([NH:10][C@@H:11]([C:45]([CH3:48])([CH3:47])[CH3:46])[C:12]([N:14]2[C@H:29]([C:30]([NH:32][C@@H:33]([CH2:42][CH2:43][CH3:44])[CH:34]([OH:41])[C:35]([NH:37][CH:38]3[CH2:40][CH2:39]3)=[O:36])=[O:31])[CH2:28][C@:16]3([O:20][C:19](=[O:21])[N:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17]3)[CH2:15]2)=[O:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH:1]1([CH2:7][C:8]([NH:10][C@@H:11]([C:45]([CH3:46])([CH3:48])[CH3:47])[C:12]([N:14]2[C@H:29]([C:30]([NH:32][C@@H:33]([CH2:42][CH2:43][CH3:44])[C:34](=[O:41])[C:35]([NH:37][CH:38]3[CH2:40][CH2:39]3)=[O:36])=[O:31])[CH2:28][C@:16]3([O:20][C:19](=[O:21])[N:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17]3)[CH2:15]2)=[O:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 59547322HCID 59547322, compound

Product 1

HCID 25124718HCID 25124718, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5S,8S)-7-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-N-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)-2-oxo-3-phenyl-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxamide (I1) (20 mg, 30 μmol, 1 eq.) was diluted in DCM. Dess Martin reagent (38 mg, 90 μmol, 3 eq.) was added and the mixture was stirred for 3 hrs at room temp. Na2S2O3 (aq., 5 eq.) was added and the mixture was stirred for another 0.5 hrs. The product was extracted with DCM. Chromatography on the combined organic layers using hexanes and ethyl acetate gave 15.9 mg (24 mot) (5S,8S)-7-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)-2-oxo-3-phenyl-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxamide (compound no. 3). 1H NMR (300 MHz, CDCl3) 7.5 (d, 2H), 7.4-7.32 (m, 2H), 7.2-7.12 (m, 2H), 6.9 (m, 1H), 6.17 (d, 1H), 5.4-5.3 (m, 1H), 4.77 (t, 1H), 4.65 (d, 1H), 4.42 (d, 1H), 4.15-3.98 (m, 2H), 3.76 (d, 1H), 2.83-2.75 (m, 1H), 2.6 (m, 2H), 2.2-0.8 (m, 31H), 0.6 (m, 2H).

Workup

  1. stirringthe mixture was stirred for another 0.5 hrs
  2. extractionThe product was extracted with DCM

Sources & evidence

ORD record
ord-ce00d036c41e4706baf19a998ab63f53
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

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