HCID 86590985, compound → HCID 59989625, compound

HRID 982660Notes

Reaction equation

HRID 982660 reaction equation
C([O:5][C:6]([C@H:8]([N:10]1[C:15](=[O:16])[C@H:14]([OH:17])[C@H:13]([OH:18])[CH2:12][O:11]1)[CH3:9])=[O:7])(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[C:6]([C@H:8]([N:10]1[C:15](=[O:16])[C@H:14]([OH:17])[C@H:13]([OH:18])[CH2:12][O:11]1)[CH3:9])([OH:7])=[O:5]

Participants

4

Reactant 1

HCID 86590985HCID 86590985, compound

Product 1

HCID 59989625HCID 59989625, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (ca. 0° C.) stirred solution of the tert-butyl ester 8b (0.0467 g, 0.179 mmol) in CH2Cl2 (0.9 ml), trifluoroacetic acid (0.9 mL) was added in one portion. The reaction mixture was kept for 1 hour at room temperature and was evaporated in vacuo to dryness. The semisolid residue was triturated with dry ether and dried in vacuo to afford 0.0295 g (80%) of the product 9b as a white solid. 1H NMR (400 MHz) in CD3CN (J, Hz): δ 1.41 (3H, d, 3J=7.3, α-MeCH), 3.60 (2H, br. s, OH, OH, COOH), 4.14 (1H, dd, 2J=−11.6, 3J=2.3, 6-HA), 4.34 (1H, d, 3J=4.1, 4-H), 4.40 (1H, dd, 2J=−11.6, 3J=7.4, 6-HB), 4.49-4.45 (2H, m, 5-H), 5.01 (1H, q, 3J=7.3, α-CH), 5.31 (1H, br. s, COOH). 13C (100 MHz) in CD3CN: δ 14.45, 54.48, 70.05, 70.99, 77.77, 167.30, 171.82.

Workup

  1. additionwas added in one portion
  2. customwas evaporated in vacuo to dryness
  3. customThe semisolid residue was triturated with dry ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1ce86b9e38544b95a49dde99828bbafb
Source dataset
uspto-grants-2005_03
Patent number
US06861416B2

Reaction notes

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