Hydrochloric Acid → tert-butyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-oxo-5-[(3-oxopropyl)amino]pentanoate

HRID 25699Notes

Reaction equation

HRID 25699 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:22]([NH:24][CH2:25][CH2:26][CH:27](OCC)[O:28]CC)=[O:23])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:22](=[O:23])[NH:24][CH2:25][CH2:26][CH:27]=[O:28])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59065896HCID 59065896, compound

Product 1

HCID 59065856tert-butyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-oxo-5-[(3-oxopropyl)amino]pentanoateYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By using an analogous procedure to that described for Reference Example 14, tert-butyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-[(3,3-diethoxypropyl)amino]-5-oxopentanoate (2.75 g, 5.9 mmol, obtained from Reference Example 25) in tetrahydrofuran (12 ml) was reacted with 0.5 N hydrochloric acid (12 ml) for 1 hour at room temperature, to provide tert-butyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-oxo-5-[(3-oxopropyl)amino]pentanoate (2.1 g, 91%) as a pale yellow solid.

Sources & evidence

ORD record
ord-29d63127da22445fadfefea43da636cd
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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