Trifluoroacetic acid → HCID 131716587, compound

HRID 1032686Notes

Reaction equation

HRID 1032686 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][C@H:16]([C:32]([N:34]1[C@H:39]([C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:41])[CH:38]2[CH2:50][CH2:51][CH:35]1[CH2:36][CH2:37]2)=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=O)(C)(C)C>C(Cl)Cl>[CH2:25]([O:24][C:22]([NH:21][CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]([C:32]([N:34]1[C@H:39]([C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:41])[CH:38]2[CH2:50][CH2:51][CH:35]1[CH2:36][CH2:37]2)=[O:33])[NH2:15])=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131716588HCID 131716588, compound

Product 1

HCID 131716587HCID 131716587, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the method of deprotection with trifluoroacetic acid in anhydrous methylene chloride, described by B. GUTTE and K. B. MERRIFIELD (J. Am. Chem. Soc. 1969, 91, 501), a quantitative yield of (3S)-2-[(S)-Nε -benzyloxycarbonyllysyl]-3-benzyloxycarbonyl-2-azabicyclo[2.2.2]octane is obtained from the (3S)-2-[(S)-Nα -tert-butoxycarbonyl-Nε -benzyloxycarbonyllysyl]-3-benzyloxycarbonyl-2-azabicyclo[2.2.2]octane prepared in the preceding stage.

Sources & evidence

ORD record
ord-092d1c3f71184e778f4a8c4c38a6c5eb
Source dataset
uspto-grants-1990_09
Patent number
US04959372

Reaction notes

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