Hydrochloric Acid → HCID 86702794, compound

HRID 1425908Notes

Reaction equation

HRID 1425908 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(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:19]([O:21]C(C)(C)C)=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6]C=C[CH:3]=1.Cl.C(O[CH2:58][CH3:59])C>CCOC(C)=O>[C:2]([C@@:18]([NH2:26])([CH2:17][CH2:16][CH2:15][N:14]([CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:59]=[CH:58][CH:3]=1)=[O:10])[CH2:41][CH2:42][NH:43][C:44]([O:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:45])[C:19]([OH:21])=[O:20])([CH3:7])([CH3:3])[CH3:1]

Participants

5

Reactant 3

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

Product 1

HCID 86702794HCID 86702794, 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 XXII (3.00 g, 4.04 mmol) in EtOAc (20 mL) was added HCl (3.5 M solution in EtOAc, 20 mL). The reaction mixture was stirred for 30 min at room temperature before adding ethyl ether (about 50 mL). The precipitate was filtered and washed with ether to give tert-butyl (2S)-5-[bis(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-2-aminopentanoic 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-4e59bb13484b48148b3f41204c8638b4
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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