Hydrochloric Acid → HCID 67520568, compound

HRID 1923976Notes

Reaction equation

HRID 1923976 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][N:14]([CH2:41][CH2:42][NH:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[CH2:15][CH2:16][CH2:17][C@H:18]([N:26]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:19]([O:21]C(C)(C)C)=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(OCC)C>C(OCC)(=O)C>[CH2:47]([O:46][C:44]([NH:43][CH2:42][CH2:41][N:14]([CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH2:15][CH2:16][CH2:17][C@H:18]([N:26]([C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:19]([OH:21])=[O:20])=[O:45])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86625798HCID 86625798, compound

Product 1

HCID 67520568HCID 67520568, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (2S)-5-[bis(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-2-{bis[(tert-butoxy)carbonyl]amino}pentanoate XXXI (3.00 g, 4.04 mmol) in ethyl acetate (20 mL) was added HCl (3.5 M solution in EtOAc, 20 mL). The reaction mixture was stirred for 30 min at r.t. before adding ethyl ether (about 50 mL). The precipitate was filtered and washed with ether to give (2S)-5-[bis(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-2-{bis[(tert-butoxy)carbonyl]amino}pentanoic acid as a white crystalline solid (1.82 g, 3.14 mmol, 78% yield).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ether

Sources & evidence

ORD record
ord-22b6ccb58bd04102b0d4ab0132e31a1e
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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