Triacetoxyperiodinane → HCID 90370359, compound

HRID 2176002Notes

Reaction equation

HRID 2176002 reaction equation
OCCC1C=C(C=CC=1)[C:7]([NH:9][C:10]1[S:11][C:12]2[CH2:39][CH2:38][CH2:37][CH2:36][C:13]=2[C:14]=1[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)=[O:16])=[O:8].CC(OI1(OC(C)=O)(OC(C)=O)O[C:54](=O)[C:53]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]1=2)=O>>[CH3:20][CH2:19][CH:18]([NH:17][CH2:15][CH2:54][C:53]1[CH:48]=[C:49]([CH:50]=[CH:51][CH:52]=1)[C:7]([NH:9][C:10]1[S:11][C:12]2[CH2:39][CH2:38][CH2:37][CH2:36][C:13]=2[C:14]=1[C:15]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:34][CH:35]=2)=[CH:22][CH:23]=1)=[O:16])=[O:8])[CH2:23][CH3:22]

Participants

3

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 90370238HCID 90370238, compound

Product 1

HCID 90370359HCID 90370359, compoundYield 185.9%

Procedure

By using 250 mg of methyl 4-[2-(4-{[(2-{[3-(2-hydroxyethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate and 450 mg of Dess-Martin Periodinane, the reaction similar to Preparation Example 2 was performed, and then the reaction similar to Preparation Example 14 was performed, thereby obtaining 260 mg of methyl 4-{2-[4-({[2-({3-[2-(pentan-3-ylamino)ethyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate.

Workup

  1. customthe reaction
  2. customsimilar to Preparation Example 2
  3. customthe reaction
  4. customsimilar to Preparation Example 14

Sources & evidence

ORD record
ord-41efaf9ea48c4febba678c4658927d17
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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