Hydrochloric Acid → HCID 22865764, compound

HRID 1779775Notes

Reaction equation

HRID 1779775 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13](=O)[C@@H:14]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:15][C@@H:16]([CH:28]([CH3:30])[CH3:29])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=1.CO.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:35]([O:34][C:32]([NH:31][C@@H:14]([CH2:15][C@@H:16]([CH:28]([CH3:30])[CH3:29])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:22][CH:23]=1)[CH:13]=[O:12])=[O:33])([CH3:38])([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21225700DiisobutylaluminumhydrideHCID 53804569HCID 53804569, compound

Product 1

HCID 22865764HCID 22865764, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

At -75° C., 4.2 ml of 1.2M diisobutylaluminium hydride solution in toluene are slowly added dropwise to a solution of 1 g of 2(S)-tert-butoxycarbonylamino-4(S)-isopropyl-5-(p-tert-butyl-phenyl)-pentanoic acid methyl ester in 20 ml of toluene. The reaction mixture is then stirred for a further 30 minutes at -70° C., 10 ml of methanol are added, the mixture is poured onto a mixture of ice and 10 ml of 1N hydrochloric acid, and extraction is carried out with ethyl acetate. The title compound is obtained: Rf (dichloromethane)=0.35.

Sources & evidence

ORD record
ord-810f1f9d12a5431499ec4fdba3cd7cac
Source dataset
uspto-grants-1997_05
Patent number
US05627182

Reaction notes

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