Hydrochloric Acid → HCID 67288735, compound

HRID 403425Notes

Reaction equation

HRID 403425 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([NH:9][C@@H:10]2[C:24](=[O:25])[N:23]3[CH2:26][C@H:27]([O:29]C(=O)C4C=CC([N+]([O-])=O)=CC=4)[CH2:28][C@H:22]3[C:21](=[O:41])[NH:20][C@:19]3([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:42][CH:18]3[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])[CH:3]=1.[Li+].[OH-].Cl>C1COCC1.ClCCl>[OH:29][C@H:27]1[CH2:26][N:23]2[C:24](=[O:25])[C@@H:10]([NH:9][C:7]([C:4]3[CH:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[O:8])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][CH:18]3[CH2:42][C@@:19]3([C:43]([O:45][CH2:46][CH3:47])=[O:44])[NH:20][C:21](=[O:41])[C@@H:22]2[CH2:28]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67290031HCID 67290031, compound

Product 1

HCID 67288735HCID 67288735, compoundYield 103.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,6S,14aR,16aS,Z)-ethyl 6-(5-methylisoxazole-3-carboxamido)-2-(4-nitrobenzoyloxy)-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]diazacyclopentadecine-14a-carboxylate (10 g) in THF (110 mL) at 0° C. was added a solution of 0.5 M LiOH (33.8 mL). After 1 h, the reaction was diluted with dichloromethane (150 mL) and neutralized with 1N HCl (50 mL). The organic layer was extracted and washed with 5% NaHCO3 (50 mL) twice and once with a 5% aq. NaCl solution (50 mL). The dichloromethane layer was evaporated under reduced pressure to an oil (8.0 g, 100% yield).

Workup

  1. extractionThe organic layer was extracted
  2. washwashed with 5% NaHCO3 (50 mL) twice

Sources & evidence

ORD record
ord-a7cc17588b654674a7125df360c41085
Source dataset
uspto-grants-2014_06
Patent number
US08748374B2

Reaction notes

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