HCID 71041830, compound → HCID 71008841, compound

HRID 1845973Notes

Reaction equation

HRID 1845973 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([CH:15]=1)=[N:13][C:12]([O:16][C@H:17]1[CH2:55][N:20]3[C:21](=[O:54])[C@@H:22]([NH:46]C(=O)OC(C)(C)C)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][C@@H:30]4[CH2:35][C@@:31]4([C:36](=[O:45])[NH:37][S:38]([C:41]4([CH3:44])[CH2:43][CH2:42]4)(=[O:40])=[O:39])[NH:32][C:33](=[O:34])[C@@H:19]3[CH2:18]1)=[C:11]1[C:6]=2[CH:7]=[CH:8][CH:9]=[CH:10]1>ClCCl.Cl.O1CCOCC1>[NH2:46][C@@H:22]1[C:21](=[O:54])[N:20]2[CH2:55][C@H:17]([O:16][C:12]3[N:13]=[C:14]4[C:5](=[C:6]5[C:11]=3[CH:10]=[CH:9][CH:8]=[CH:7]5)[CH:4]=[CH:3][C:2]([F:1])=[CH:15]4)[CH2:18][C@H:19]2[C:33](=[O:34])[NH:32][C@:31]2([C:36]([NH:37][S:38]([C:41]3([CH3:44])[CH2:42][CH2:43]3)(=[O:39])=[O:40])=[O:45])[CH2:35][C@H:30]2[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 1

HCID 71041830HCID 71041830, compound

Product 1

HCID 71008841HCID 71008841, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of the product of Example 1h (tert-butyl (2R,6S,13aS,14aR,16aS,Z)-2-(3-fluorophenanthridin-6-yloxy)-14a-(1-methylcyclopropylsulfonylcarbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-ylcarbamate, 16.0 g, 20.6 mmol) in dichloromethane (100 mL) and 4 N HCl in dioxane (100 mL) was stirred at room temperature for 90 min and then evaporated under reduced pressure. The residue was partitioned between ethyl acetate (200 mL) and saturated aqueous sodium bicarbonate solution (200 mL) and the resulting solid isolated by filtration of the mixture through a medium porosity sintered glass funnel. The isolated solid was washed with water (2×150 mL) and dried under reduced pressure to provide the title compound (12.2 g, 88% yield).

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate (200 mL) and saturated aqueous sodium bicarbonate solution (200 mL)
  3. customthe resulting solid isolated by filtration of the mixture through a medium porosity sintered glass funnel
  4. washThe isolated solid was washed with water (2×150 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f25b82a43a284ebea6781c89c260553a
Source dataset
uspto-grants-2015_02
Patent number
US08951964B2

Reaction notes

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