Triacetoxyperiodinane → HCID 57526838, compound

HRID 1452639Notes

Reaction equation

HRID 1452639 reaction equation
[C:1]([O:5][C:6]([N:8]([C:44]1[CH:49]=[CH:48][C:47]([O:50][CH2:51][CH3:52])=[CH:46][CH:45]=1)[C:9]1[N:14]2[N:15]=[CH:16][CH:17]=[C:13]2[N:12]=[C:11]([NH:18][C@H:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]2)[C:10]=1[CH2:32][CH:33](O)[CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([C:44]1[CH:49]=[CH:48][C:47]([O:50][CH2:51][CH3:52])=[CH:46][CH:45]=1)[C:9]1[N:14]2[C:13](=[CH:17][CH:16]=[N:15]2)[N:12]=[C:11]2[C:10]=1[CH:32]=[C:33]([CH2:34][O:35][Si:36]([C:39]([CH3:40])([CH3:41])[CH3:42])([CH3:37])[CH3:38])[N:18]2[C@H:19]1[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:20]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57526796HCID 57526796, compound

Product 1

HCID 57526838HCID 57526838, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (1 mL) solution containing tert-butyl (S)-3-{7-[tert-butoxycarbonyl-(4-ethoxyphenyl)amino]-6-[3-(tert-butyldimethylsilanyloxy)-2-hydroxypropyl]pyrazolo[1,5-a]pyrimidin-5-ylamino}piperidine-1-carboxylate (28.6 mg, 0.0495 mmol), Dess-Martin periodinane (25.2 mg, 0.0594 mmol) was added at 0° C., and the mixture was allowed to warm to room temperature and stirred for 3 hr. After the reaction, the reaction solution was concentrated, and the residue was purified with PTLC (30% ethyl acetate-hexane) to obtain the title compound (14.5 mg).

Workup

  1. additionwas added at 0° C.
  2. customAfter the reaction
  3. concentrationthe reaction solution was concentrated
  4. customthe residue was purified with PTLC (30% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-30a8998a5cbd4bdcb2c98947485f479a
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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