Hydrochloric Acid → HCID 86626942, compound

HRID 1695318Notes

Reaction equation

HRID 1695318 reaction equation
[C:1]([O:5][C:6](=[O:60])[N:7]([CH2:34][CH2:35][O:36][C:37]1[CH:42]=[C:41]([O:43][CH3:44])[C:40]([C:45]([N:47]2[CH2:51][C:50](=[CH2:52])[CH2:49][C@H:48]2[C:53](OC)=[O:54])=[O:46])=[CH:39][C:38]=1[N+:57]([O-:59])=[O:58])[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([C:19]([N:21]2[CH2:25][C:24](=[CH2:26])[CH2:23][C@H:22]2[C:27](OC)=[O:28])=[O:20])=[CH:13][C:12]=1[N+:31]([O-:33])=[O:32])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.Cl>C1(C)C=CC=CC=1.CO>[C:1]([O:5][C:6](=[O:60])[N:7]([CH2:34][CH2:35][O:36][C:37]1[CH:42]=[C:41]([O:43][CH3:44])[C:40]([C:45]([N:47]2[CH2:51][C:50](=[CH2:52])[CH2:49][C@H:48]2[CH:53]=[O:54])=[O:46])=[CH:39][C:38]=1[N+:57]([O-:59])=[O:58])[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([C:19]([N:21]2[CH2:25][C:24](=[CH2:26])[CH2:23][C@H:22]2[CH:27]=[O:28])=[O:20])=[CH:13][C:12]=1[N+:31]([O-:33])=[O:32])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 86626943HCID 86626943, compound

Product 1

HCID 86626942HCID 86626942, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a vigorously stirred solution of bis{2-[5-methoxy-2-nitro-4-[(S)-4-methylene-2-methoxycarbonyl-1-pyrrolidinylcarbonyl]phenyloxy]-ethyl}-carbamic acid tert-butyl ester 12 (100 mg, 0.12 mmol) in anhydrous toluene (2.4 mL) was added dropwise solution of DIBAL-H (480 μL of a 1M solution in toluene) at −78° C. under argon atmosphere. After the mixture was stirred for an additional 45 min, excess reagent was decomposed by addition of five drops of methanol followed by 5% HCl (4 mL). The resulting mixture was allowed to warm to 0° C. Layers were separated and the aqueous layer was further extracted with CH2Cl2 (3×3 mL). Combined organic layers were washed with brine, dried (MgSO4) and concentrated. Purification of the residue by flash chromatography (silica gel, 95:5 CHCl3/MeOH) yielded bis{2-[5-methoxy-2-nitro-4-[(S)-4-methylene-2-formyl-1-pyrrolidinylcarbonyl]phenyloxy]-ethyl}-carbamic acid tert-butyl ester 13 as light yellow oil (84 mg, 91%).

Workup

  1. customLayers were separated
  2. extractionthe aqueous layer was further extracted with CH2Cl2 (3×3 mL)
  3. washCombined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification of the residue by flash chromatography (silica gel, 95:5 CHCl3/MeOH)

Sources & evidence

ORD record
ord-f73f7cb472764b62a603c8382e5a32b6
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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