Hydrochloric Acid → HCID 70295854, compound

HRID 1872792Notes

Reaction equation

HRID 1872792 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][CH2:13][C@H:14]([NH:36]C(OC(C)(C)C)=O)[C:15]([O:17][C@@H:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:19][C:20]([NH2:22])=[O:21])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:44]>C(OCC)(=O)C.C(OCC)C>[ClH:44].[CH2:1]([O:8][C:9]([CH2:11][CH2:12][CH2:13][C@H:14]([NH2:36])[C:15]([O:17][C@@H:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:19][C:20]([NH2:22])=[O:21])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21970279HCID 21970279, compound

Product 1

HCID 70295854HCID 70295854, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3S)-3-[(2S)-5-benzyloxycarbonyl-2-(tertiarybutoxycarbonylamino)pentanoyl]oxyhexadecanamide (4.90 g) in 4N hydrogen chloride in ethyl acetate (10 ml) was stirred at room temperature for an hour, and then at 0° C. for an additional one hour. This solution was diluted with diethyl ether (25 ml). The resulting precipitate was collected by filtration, and washed with diethyl ether (30 ml). This crystalline solid was dried over potassium hydroxide under vacuum to yield (3S)-3-[(2S)-5-benzyloxycarbonyl-2-aminopentanoyl)oxyhexadecanamide hydrochloride (4.35 g).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with diethyl ether (30 ml)
  3. dry with materialThis crystalline solid was dried over potassium hydroxide under vacuum

Sources & evidence

ORD record
ord-367e89c00a384cabae43e20cfb750a1f
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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