Benzyl chloroformate → (S,S)-2,7-Bis(tert-butyloxycarbonylamino)-4-benzyloxycarbonyl-4-azaoctanedioic acid

HRID 976024Notes

Reaction equation

C([O-])(O)=O.[Na+].[CH2:6]([O:13][C:14](Cl)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:17]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][NH:30][CH2:31][CH2:32][C@H:33]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:34]([OH:36])=[O:35])[C:26]([OH:28])=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18]>O1CCOCC1.O>[C:17]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][N:30]([C:14]([O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:15])[CH2:31][CH2:32][C@H:33]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:34]([OH:36])=[O:35])[C:26]([OH:28])=[O:27])=[O:23])([CH3:19])([CH3:20])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

1M NaHCO3 (5.9 ml, 5.92 mmol ) and benzyloxycarbonyl chloride (0.5 g, 0.42 ml, 2.96 mmol) were added to a solution of (S,S)-2,7-bis (tert-butyloxycarbonylamino)-4-azaoctanedioic acid (0.6 g, 1.48 mmol) in dioxane (40 ml ) and H2O (30 ml ) at 0° C. The mixture was stirred at 0° C. for 3 hours, at ambient temperature for 6 hours, evaporated, the residue triturated with chloroform (5 ml) and acetic acid to pH 5. The chloroform solution was evaporated and the product isolated after chromatography on silica gel (CHCl3 : MeOH 4:1).

Workup

customevaporated
customthe residue triturated with chloroform (5 ml) and acetic acid to pH 5
customThe chloroform solution was evaporated
customthe product isolated after chromatography on silica gel (CHCl3 : MeOH 4:1)

Sources & evidence

ORD record: ord-3c82f7f9457e42389d94d1091b384c90
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05610141

Reaction notes

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