Trifluoroacetic acid → (2s,4s)-Methyl 4-azido-1-((s)-2-((s)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylate

HRID 237241Notes

Reaction equation

HRID 237241 reaction equation
[N:1]([C@@H:4]1[CH2:8][N:7]([C:9](=[O:23])[C@@H:10]([NH:15][C:16](OC(C)(C)C)=[O:17])[C:11]([CH3:14])([CH3:13])[CH3:12])[C@H:6]([C:24]([O:26][CH3:27])=[O:25])[CH2:5]1)=[N+:2]=[N-:3].FC(F)(F)C(O)=O.[N:35]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])([CH3:41])[C@H:36](C(O)=O)[CH3:37]>>[N:1]([C@@H:4]1[CH2:8][N:7]([C:9](=[O:23])[C@@H:10]([NH:15][C:16](=[O:17])[C@@H:36]([N:35]([C:42]([O:44][C:45]([CH3:46])([CH3:48])[CH3:47])=[O:43])[CH3:41])[CH3:37])[C:11]([CH3:12])([CH3:13])[CH3:14])[C@H:6]([C:24]([O:26][CH3:27])=[O:25])[CH2:5]1)=[N+:2]=[N-:3]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 57661035(2s,4s)-Methyl 4-azido-1-((s)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylate

Product 1

HCID 57661019(2s,4s)-Methyl 4-azido-1-((s)-2-((s)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylate

Procedure

The title compound of Example 1 was treated with trifluoroacetic acid using the general procedure A to deprotect the BOC group. The resulting trifluoroacetic acid salt was coupled to Boc-N-Me-Ala-OH using the general procedure D to prepare the title compound of Example 2. 1H NMR (CDCl3): consistent with proposed structure.

Sources & evidence

ORD record
ord-10a7f6fc613245f38e6fe1fe9362ea29
Source dataset
uspto-grants-2014_02
Patent number
US08642554B2

Reaction notes

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