Hydrochloric Acid → HCID 69744946, compound

HRID 1063914Notes

Reaction equation

HRID 1063914 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C@:12]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])([C:15]2[S:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH3:28])=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)[S:11](=[O:38])(=[O:37])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:26]([C:23]1[CH:22]=[CH:21][C:20]([C:17]2[S:16][C:15]([C@:12]3([CH2:29][C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[S:11](=[O:38])(=[O:37])[CH2:10][CH2:9][NH:8][CH2:14][CH2:13]3)=[CH:19][CH:18]=2)=[CH:25][CH:24]=1)[CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 69744461HCID 69744461, compound

Product 1

HCID 69744946HCID 69744946, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of t-butyl 2-[(S)-4-t-butoxycarbonyl-7-(5-(4-propylphenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate (10.4 g) in tetrahydrofuran (120 ml) was added conc. hydrochloric acid (30 ml) in tetrahydrofuran (30 ml) under ice-water cooling and the mixture was stirred at ambient temperature for 15 hours. The mixture was basified with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated in vacuo to give t-butyl 2-[(S)-7-(5-(4-propylphenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate (8.94 g) as yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-355296f64b574e6893d359cc3443568d
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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