Trifluoroacetic acid → HCID 57500393, compound

HRID 2273548Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:46]=[CH:47][CH:48]=1)[C:8]([NH:10][C:11]1[C:12]([CH3:45])=[C:13]([C:20]([C:22]2[CH:23]=[CH:24][C:25]([NH:38][C:39](=[O:44])[C:40]([F:43])([F:42])[F:41])=[C:26]([CH:37]=2)[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])=[O:21])[N:14]2[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]2)=[O:9].C(OC([NH:56][CH2:57][C:58](O)=[O:59])=O)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:56][CH2:57][C:58]([NH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:46]=[CH:47][CH:48]=1)[C:8]([NH:10][C:11]1[C:12]([CH3:45])=[C:13]([C:20]([C:22]2[CH:23]=[CH:24][C:25]([NH:38][C:39](=[O:44])[C:40]([F:41])([F:42])[F:43])=[C:26]([CH:37]=2)[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])=[O:21])[N:14]2[C:19]=1[CH:18]=[CH:17][CH:16]=[CH:15]2)=[O:9])=[O:59]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 78288N-(tert-butoxycarbonyl)glycine

HCID 57500374HCID 57500374, compound

Product 1

HCID 57500393HCID 57500393, compound

Procedure

By following the process described in stage G of Example 42, the coupling of benzyl 5-[(1-{[3-(2-aminoethoxy)benzoyl]amino}-2-methylindolizin-3-yl)carbonyl]-2-[(trifluoroacetyl)amino]benzoate (described in stage F, Example 42) with N-tert-butoxycarbonylglycine is carried out. The compound obtained is then deprotected with trifluoroacetic acid to give the amine according to the process described in stage F of Example 42.

Workup

customThe compound obtained

Sources & evidence

ORD record: ord-ae1b9327c5e94d3baa0761b21c12fd3a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120819B2

Reaction notes

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