Ethyl Acetate → HCID 86650245, compound

HRID 2371329Notes

Reaction equation

HRID 2371329 reaction equation
C[O:2][C:3]([C@H:5]1[NH:21][C:20](=[O:22])[C@H:19]([CH:23]([CH3:25])[CH3:24])[NH:18][C:17](=[O:26])[C@@H:16]([NH:27][C:28]([C:30]2[NH:31][CH:32]=[CH:33][CH:34]=2)=[O:29])[CH2:15][C:14]2=[CH:35][CH:36]=[C:11]([CH:12]=[CH:13]2)[O:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=O.CC(C[AlH]CC(C)C)C.CCOC(C)=O>C(Cl)Cl>[CH:3]([C@H:5]1[NH:21][C:20](=[O:22])[C@H:19]([CH:23]([CH3:25])[CH3:24])[NH:18][C:17](=[O:26])[C@@H:16]([NH:27][C:28]([C:30]2[NH:31][CH:32]=[CH:33][CH:34]=2)=[O:29])[CH2:15][C:14]2=[CH:13][CH:12]=[C:11]([CH:36]=[CH:35]2)[O:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 66846964(7S,10S,13S)-10-Isopropyl-9,12-dioxo-13-[(1H-pyrrole-2-carbonyl)-amino]-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-7-carboxylic acid methyl ester

Product 1

HCID 86650245HCID 86650245, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Ester 51 (45 mg) was dissolved in DCM (6 mL) under an atmosphere of argon. The reaction was cooled to −78° C. To the resultant solution DIBAL (0.5 mL) was added dropwise. This was stirred for 2 h before being allowed to warm to rt overnight. The reaction mixture was partitioned between EtOAc and 1M hydrochloric acid. The aqueous phase was extracted again with EtOAc and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 1/1 EtOAc/(50/70) petroleum ether to EtOAc to yield a light brown solid, 14 mg, 33%. Rf=0.25 (1/1 EtOAc/(50/70) petroleum ether).

Workup

  1. temperatureto warm to rt overnight
  2. customThe reaction mixture was partitioned between EtOAc and 1M hydrochloric acid
  3. extractionThe aqueous phase was extracted again with EtOAc
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification
  8. washeluting with a gradient of 1/1 EtOAc/(50/70) petroleum ether to EtOAc
  9. customto yield a light brown solid, 14 mg, 33%

Sources & evidence

ORD record
ord-ab217bbab05b4c32a1382387a05c8810
Source dataset
uspto-grants-2014_04
Patent number
US08710178B2

Reaction notes

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