Trifluoroacetic acid → Trifluoroacetic acid

HRID 1056403Notes

Reaction equation

C(OC([NH:8][C@@H:9]([C:12]1[N:13]([S:24]([C:27]2[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:14]=[CH:15][C:16]=1[C:17]([O:19]C(C)(C)C)=[O:18])[CH2:10][CH3:11])=O)(C)(C)C.[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>C(Cl)Cl>[NH2:8][C@@H:9]([C:12]1[N:13]([S:24]([C:27]2[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=2)(=[O:26])=[O:25])[CH:14]=[CH:15][C:16]=1[C:17]([OH:19])=[O:18])[CH2:10][CH3:11].[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35].[F:37][C:36]([F:39])([F:38])[C:34]([OH:40])=[O:35].[NH2:8][C@@H:9]([C:12]1[N:13]([S:24]([C:27]2[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=2)(=[O:26])=[O:25])[CH:14]=[CH:15][C:16]=1[C:17]([OH:19])=[O:18])[CH2:10][CH3:11]

Participants

Conditions

Temperature: 40 °C

Procedure

An orange solution of (R)-tert-butyl 2-(1-((tert-butoxycarbonyl)amino)propyl)-1-tosyl-1H-pyrrole-3-carboxylate (505c, 6.19 g, 12.93 mmol) in DCM (15 mL) was treated with TFA (15 mL, 202 mmol) and heated at 40° C. for 4 h. The TFA and DCM was removed in vacuo affording (R)-2-(1-aminopropyl)-1-tosyl-1H-pyrrole-3-carboxylic acid compound with TFA (1:1) as a viscous orange oil (505d) which was used the next step without further purification. m/z (ESI, +ve) 323.1 (M+1)′.

Workup

customThe TFA and DCM was removed in vacuo

Sources & evidence

ORD record: ord-227ac907f8a54d81a0b2126778b4a496
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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