m-Chloroperbenzoic acid → HCID 67325455, compound

HRID 1616947Notes

Reaction equation

HRID 1616947 reaction equation
Cl.FC1C=C([S:13]([C:16]2[CH:28]=[CH:27][C:19]3[CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH:21]4[O:26][C:18]=3[CH:17]=2)(=[O:15])=[O:14])C=C(OC(C)C)C=1.[CH2:29]([O:36][C:37]1[CH:42]=[C:41]([O:43][CH:44]([CH3:46])[CH3:45])[CH:40]=[C:39](I)[CH:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CC([Si](SC1C=CC2C3CCN([C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])CC3OC=2C=1)(C(C)C)C(C)C)C.[S].C1C=C(Cl)C=C(C(OO)=O)C=1.C(OC(N1CCC2C3C=C(S(C4C=CC=C(Cl)C=4)(=O)=O)C=CC=3OC2C1)=O)(C)(C)C>>[C:74]([O:73][C:71]([N:23]1[CH2:24][CH2:25][CH:20]2[C:19]3[CH:27]=[CH:28][C:16]([S:13]([C:39]4[CH:40]=[C:41]([O:43][CH:44]([CH3:46])[CH3:45])[CH:42]=[C:37]([O:36][CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH:38]=4)(=[O:14])=[O:15])=[CH:17][C:18]=3[O:26][CH:21]2[CH2:22]1)=[O:72])([CH3:77])([CH3:76])[CH3:75]

Participants

7

Reactant 6

HCID 70297m-Chloroperbenzoic acidHCID 5362487SulfurHCID 67322940HCID 67322940, compoundHCID 67323482HCID 67323482, compoundHCID 67324723HCID 67324723, compoundHCID 67324860HCID 67324860, compound

Product 1

HCID 67325455HCID 67325455, compound

Procedure

Prepared as described for 7-(3-Fluoro-5-isopropoxy-benzenesulfonyl)-1,2,3,4,4a,9a-hexahydro-benzo[4,5]furo[2,3-c]pyridine hydrochloride starting from 1-(benzyloxy)-3-iodo-5-(propan-2-yloxy)benzene and tert-butyl 7-[(tripropan-2-ylsilyl)sulfanyl]-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate C02. Sulfur oxidation was performed with mCPBA as described for 6-(3-chloro-benzenesulfonyl)-3,4,4a,9a-tetrahydro-1H-benzo[4,5]furo[2,3-c]pyridine-2-carboxylic acid tert-butyl ester.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7362bf9bea7947daa59035fdf5bc3c2d
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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