Triacetoxyperiodinane → HCID 11519899, compound

HRID 1867624Notes

Reaction equation

HRID 1867624 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O:23]=[C:24]1[C@H:30]([NH:31][C:32]([N:34]2[CH2:39][CH2:38][CH:37]([NH:40][C:41]([NH:43][C@H:44]([C:47]([O:49][CH3:50])=[O:48])[CH2:45]O)=[O:42])[CH2:36][CH2:35]2)=[O:33])[N:29]=[C:28]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:27]2[CH:57]=[CH:58][CH:59]=[CH:60][C:26]=2[N:25]1[CH2:61][C:62]([F:65])([F:64])[F:63]>ClCCl>[O:42]=[C:41]1[NH:43][C:44]([C:47]([O:49][CH3:50])=[O:48])=[CH:45][N:40]1[CH:37]1[CH2:38][CH2:39][N:34]([C:32]([NH:31][C@@H:30]2[N:29]=[C:28]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:27]3[CH:57]=[CH:58][CH:59]=[CH:60][C:26]=3[N:25]([CH2:61][C:62]([F:65])([F:64])[F:63])[C:24]2=[O:23])=[O:33])[CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68565136HCID 68565136, compound

Product 1

HCID 11519899HCID 11519899, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (126 mg, 0.298 mmol) was added to a solution of methyl N-({[1-({[(3R)-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]amino}carbonyl)piperidin-4-yl]amino}carbonyl)serinate (75 mg, 0.124 mmol) in dichloromethane (15 mL) at 0° C. The reaction warmed to ambient temperature, stirred for 4 h, and was quenched with a 1:1 mixture of saturated sodium thiosulfate and sodium bicarbonate solution. The mixture was extracted with dichloromethane (2×) and the combined organic extracts were dried over sodium sulfate, filtered, concentrated. Purification by silica gel chromatography (100% dichloromethane→8% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (55 mg). MS 585.4 (M+1)

Workup

  1. customwas quenched with a 1:1 mixture of saturated sodium thiosulfate and sodium bicarbonate solution
  2. extractionThe mixture was extracted with dichloromethane (2×)
  3. dry with materialthe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% dichloromethane→8% methanol {1% ammonium hydroxide}/dichloromethane)

Sources & evidence

ORD record
ord-bd76f5938b634cf3a4aefbe3b3ab5d5b
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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