Hydrochloric Acid → Hydrochloric Acid

HRID 1429093Notes

Reaction equation

HRID 1429093 reaction equation
C(OC([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:29]3[N:30]=[C:31]4[C:36](=[C:37]5[C:42]=3[CH:41]=[CH:40][CH:39]=[CH:38]5)[CH:35]=[CH:34][CH:33]=[CH:32]4)[CH2:27][C@H:21]2[C:20](=[O:43])[NH:19][C@:18]2([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:44][C@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=O)(C)(C)C.[ClH:50].O1CCOCC1>C(OCC)(=O)C>[NH2:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:29]3[N:30]=[C:31]4[C:36](=[C:37]5[C:42]=3[CH:41]=[CH:40][CH:39]=[CH:38]5)[CH:35]=[CH:34][CH:33]=[CH:32]4)[CH2:27][C@H:21]2[C:20](=[O:43])[NH:19][C@:18]2([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:44][C@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[ClH:50]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68499992HCID 68499992, compound

Product 2

HCID 313Hydrochloric AcidYield 98%HCID 68008345HCID 68008345, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,6S,13aS,14aR,16aS,Z)-ethyl 6-(tert-butoxycarbonylamino)-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo [1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (Example 18a, 6.25 g, 9.32 mmol) dissolved in Ethyl acetate (50 ml) was added 4 N hydrogen chloride in dioxane (44.3 ml, 177 mmol) and the reaction mixture was stirred at rt for 6 h. The solvent was evaporated under reduced pressure to give a white solid which was rinsed with ethyl acetate. The filtered solid was dried to give (2R,6S,13aS,14aR,16aS,Z)-ethyl 6-amino-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo [1,2-a][1,4]diazacyclopentadecine-14a-carboxylate, Hydrochloric Acid (5.52 g, 98% yield)

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto give a white solid which
  3. washwas rinsed with ethyl acetate
  4. customThe filtered solid was dried

Sources & evidence

ORD record
ord-37ddcb5b39db476db2096cb3c4bf8756
Source dataset
uspto-grants-2015_01
Patent number
US08937041B2

Reaction notes

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