Ethyl orthoformate → HCID 66870411, compound

HRID 1994373Notes

Reaction equation

HRID 1994373 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:16]([C:17](=[O:30])[NH:18][C@H:19](C=O)[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:15]2[CH2:31][C@H:12]1[CH2:13][CH2:14]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:32]([O:39][CH2:40][CH3:41])([O:36][CH2:37][CH3:38])OCC.C(=O)(O)[O-].[Na+]>ClCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:8][C:9]([N:11]1[C@H:16]([C:17](=[O:30])[NH:18][C@@H:19]([CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH:32]([O:36][CH2:37][CH3:38])[O:39][CH2:40][CH3:41])[C@@H:15]2[CH2:31][C@H:12]1[CH2:13][CH2:14]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 86601041HCID 86601041, compound

Product 1

HCID 66870411HCID 66870411, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,3S,4S)-3-((S)-2-tert-Butoxycarbonyl-1-formyl-ethylcarbamoyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester (698 mg) in dichloromethane (10 ml) was added triethyl orthoformate (720 mg) and p-toluenesulfonic acid monohydrate (6 mg). The resulting mixture was stirred at ambient temperature until no aldehyde remained by TLC. Saturated aqueous sodium bicarbonate solution was then added and the organic phase removed. This was washed with water and brine, dried (magnesium sulfate), filtered and concentrated under reduced pressure. This gave the sub-title compound as a pale yellow oil (635 mg, 78%); 1H NMR (400 MHz, d-6 DMSO) δ 0.96-1.15 (6H, m), 1.26-1.84 (16H, m), 2.20-2.50 (2H, m), 3.40-3.81 (5H, m), 4.10-4.28 (2H, m), 4.37 (1H, m), 4.88-5.14 (2H, m), 7.20-7.40 (5H, m), 7.65 (0.5H, d), 7.80 (0.5H, d).

Workup

  1. customthe organic phase removed
  2. washThis was washed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-861df288913b4232bae181fb682d1c14
Source dataset
uspto-grants-2010_01
Patent number
US07652153B2

Reaction notes

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