Hydrochloric Acid → HCID 67288735, compound

HRID 403415Notes

Reaction equation

HRID 403415 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.C1COCC1.[Li+].[OH-].Cl>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 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67290031HCID 67290031, compound

Product 1

HCID 67288735HCID 67288735, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

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 (64.6 g solution, 15.5% w/w solution in THF, 10 g starting material) was added THF (34 mL). The solution was then cooled to 0° C. and a solution of 0.5M LiOH (33.8 mL) was added dropwise keeping the temperature below 5° C. After 1 hour, 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 and diluted with THF (41 g) to give a solution. Analysis by HPLC indicated a yield of 7.8 g of the title compound (100%).

Workup

  1. customthe temperature below 5° C
  2. extractionThe organic layer was extracted
  3. washwashed with 5% NaHCO3 (50 mL) twice
  4. customThe dichloromethane layer was evaporated under reduced pressure
  5. additiondiluted with THF (41 g)
  6. customto give a solution

Sources & evidence

ORD record
ord-a1a3ac3958af44ffa299f97137f8f7d5
Source dataset
uspto-grants-2014_06
Patent number
US08748374B2

Reaction notes

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