Hydrochloric Acid → HCID 18442435, compound

HRID 458942Notes

Reaction equation

HRID 458942 reaction equation
[O:1]=[S:2]1(=[O:42])[C:8]2[CH:9]=[C:10]([O:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH:11]=[CH:12][C:7]=2[N:6]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:22][CH:21]=2)[CH2:5][C:4]([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:3]1.O.[Li+].[OH-].Cl>C1COCC1>[O:42]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:13][CH2:14][C:15]([OH:17])=[O:16])[CH:11]=[CH:12][C:7]=2[N:6]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])=[CH:22][CH:21]=2)[CH2:5][C:4]([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 3939Lithium HydroxideHCID 18442436HCID 18442436, compound

Product 1

HCID 18442435HCID 18442435, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1-Dioxo-3,3-dibutyl-5-(4-t-butoxycarbonylaminophenyl)-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 108; 607 mg, 1.0 mmol) was dissolved in THF (6 ml), H2O (6 ml) and LiOH (127 mg, 3.02 mmol, monohydrate) was added. The mixture was stirred for 1 hour. The mixture was poured into water and the solution was acidified using HCl-solution (aq, 1M). The water layer was extracted two times with EtOAc. The combined organic layer was wash once with brine, dried, filtered and evaporated under reduced pressure to give the title compound 0.571 g (99%). M/z 575.4.

Workup

  1. extractionThe water layer was extracted two times with EtOAc
  2. washThe combined organic layer was wash once with brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a69b4a56e57d4bb7bbb2ddfd0230cef4
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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