Hydrochloric Acid → HCID 57443730, compound

HRID 507438Notes

Reaction equation

HRID 507438 reaction equation
C[O:2][C:3](=[O:22])[C:4]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][CH:6]=[O:7].[Li+].[OH-].Cl>C1COCC1>[C:18]([O:17][C:15](=[O:16])[NH:14][C:4]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH:6]([OH:7])[O:2][C:3]1=[O:22])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21357710HCID 21357710, compound

Product 1

HCID 57443730HCID 57443730, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 13 (6.14 g, 20 mmol) in THF (50 mL), 3N LiOH solution (20 mL, 60 mmol) was added. After stirring for 1 h, the resulting mixture was adjusted to pH=5-6 using 1N HCl, and extracted with ethyl acetate. The combined organic phases were concentrated to afford compound 14 (5.6 g, 95.6%). 1H NMR (400 MHz, CDCl3) δ 1.43 (s, 9 H), 2.85-2.87 (m, 1 H), 3.17-3.19 (m, 1 H), 5.74-6.11 (bs, 2 H), 7.34-7.46 (m, 5 H).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe combined organic phases were concentrated

Sources & evidence

ORD record
ord-20c8b3b519604ee4a0e529366b5916c2
Source dataset
uspto-grants-2010_08
Patent number
US07786163B2

Reaction notes

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