HCID 59989618, compound → HCID 59989624, compound

HRID 982659Notes

Reaction equation

HRID 982659 reaction equation
C([O:8][C:9]([C@H:11]([N:13]1[C:18](=[O:19])[C@@H:17]([OH:20])[C@@H:16]([OH:21])[CH2:15][O:14]1)[CH3:12])=[O:10])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:9]([C@H:11]([N:13]1[C:18](=[O:19])[C@@H:17]([OH:20])[C@@H:16]([OH:21])[CH2:15][O:14]1)[CH3:12])([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 59989618HCID 59989618, compound

Product 1

HCID 59989624HCID 59989624, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A suspension of 5% Pd-C (0.137 g) in EtOAc (10 mL) was stirred for 1 h under H2 atmosphere and a solution of the benzyl ester 8a (0.137 g, 0.464 mmol) in EtOAc (15 ml) was added portionwise. The reaction mixture was stirred for 8 hours under H2 and filtered through a short pad of Silica Gel 60H (for TLC) followed by washing with MeOH (7×5 mL). After evaporation of the filtrate in vacuo, the residue was triturated with dry ether and dried in vacuo to provide 0.093 g (98%) of the product 9a as a white solid. 1H NMR (400 MHz) in CD3CN (J, Hz): δ 1.44 (3H, d, 3J=7.3, α-MeCH), 3.00 (2H, br. s, OH, OH), 3.90 (1H, m, 6-HA), 4.37 (1H, d, 3J=4.4, 4-H), 4.49-4.43 (2H, m, 6-HB, 5-H), 5.01 (1H, q, 3J=7.3, α-CH), 5.31 (1H, br. s, COOH). 13C (100 MHz) in CD3CN: δ 13.55, 54.34, 70.15, 70.64, 78.41, 171.22, 172.85.

Workup

  1. stirringThe reaction mixture was stirred for 8 hours under H2
  2. filtrationfiltered through a short pad of Silica Gel 60H (for TLC)
  3. washby washing with MeOH (7×5 mL)
  4. customAfter evaporation of the filtrate in vacuo
  5. customthe residue was triturated with dry ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6c80eaaa2dad4150882997a41200edff
Source dataset
uspto-grants-2005_03
Patent number
US06861416B2

Reaction notes

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