Hydrochloric Acid → HCID 73057818, compound

HRID 1055434Notes

Reaction equation

HRID 1055434 reaction equation
[ClH:1].C(O[C:7](=O)[N:8]([C@H:10]([C:12](=[O:46])[NH:13][C@H:14]1[CH2:20][S:19][C:18]2[C:21]([NH:25][C:26](=[O:33])[CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:22][CH:23]=[CH:24][C:17]=2[N:16]([CH2:34][C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=[CH:37][CH:36]=2)[C:15]1=[O:45])[CH3:11])C)(C)(C)C>O1CCOCC1>[ClH:1].[CH3:32][O:31][CH2:30][CH2:29][O:28][CH2:27][C:26]([NH:25][C:21]1[C:18]2[S:19][CH2:20][C@H:14]([NH:13][C:12](=[O:46])[C@@H:10]([NH:8][CH3:7])[CH3:11])[C:15](=[O:45])[N:16]([CH2:34][C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][CH:36]=3)[C:17]=2[CH:24]=[CH:23][CH:22]=1)=[O:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90037651HCID 90037651, compound

Product 1

HCID 73057818HCID 73057818, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride gas was bubbled into a solution of ((S)-1-{(R)-9-[2-(2-methoxy-ethoxy)-acetylamino]-5-naphthalen-1-ylmethyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester (70 mg, 108 μmol) in dioxane (5 mL) at 0° C. for 1 min, the mixture was warmed to RT and stirred for 1 h. The mixture was concentrated, the residue was triturated with Et2O and the resulting solid was filtered, washed with Et2O and dried to give the title compound (25 mg, 40%). HR-MS: calcd for C29H34N4O5S (MH+) 551.2326. found 551.2323.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated with Et2O
  3. filtrationthe resulting solid was filtered
  4. washwashed with Et2O
  5. customdried

Sources & evidence

ORD record
ord-3fa1ab72324a4341bb3f81ad3f094f4f
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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