Hydrochloric Acid → HCID 131715644, compound

HRID 1165356Notes

Reaction equation

HRID 1165356 reaction equation
[C:1]([C:8]([NH2:39])([CH2:19][CH2:20][CH2:21][C:22]1([CH2:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:9]([O:11]CC1C=CC=CC=1)=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+].Cl>O1CCOCC1>[C:1]([C:8]([NH2:39])([CH2:19][CH2:20][CH2:21][C:22]1([CH2:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[C:9]([OH:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131715643HCID 131715643, compound

Product 1

HCID 131715644HCID 131715644, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The Boc-diester (I) (1.27 g, 2.36 mmol) was dissolved in dioxane (15 ml) and treated with 2.6 ml 1N sodium hydroxide solution at room temperature under argon for 4 hours. The reaction mixture was acidified (pH=2) with 3N hydrochloric acid and evaporated at reduced pressure. The residue was dissolved in ethyl acetate, washed with 3N hydrochloric acid, dried over MgSO4 and evaporated at reduced pressure. The residue was purified by flash chromatography (silica gel, 5% methanol/chloroform) to give 1.03 g of the title product: MS: MH+ =448); 1HNM (CDCl3): 7.33 (S, 5H), 5.07 (S, 2H), 5.20-4.80 (m, 1H), 4.42-4.05 (m, 1H), 2.32 (S, 2H), 1.43 (S, 9H) and 2.08-1.07 (m, 16H).

Workup

  1. customevaporated at reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 3N hydrochloric acid
  4. dry with materialdried over MgSO4
  5. customevaporated at reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, 5% methanol/chloroform)

Sources & evidence

ORD record
ord-ffeb4928061a4511a9edc6799c64580a
Source dataset
uspto-grants-1990_03
Patent number
US04908475

Reaction notes

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