Trifluoroacetic acid → HCID 131736418, compound

HRID 1056128Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([C:20]1[N:21]([S:32]([C:35]2[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[CH:22]=[CH:23][C:24]=1[C:25]([O:27]C(C)(C)C)=[O:26])[NH:12]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43]>C(Cl)Cl>[F:45][C:44]([F:47])([F:46])[C:42]([OH:48])=[O:43].[NH2:12][C@@H:11]([C:20]1[N:21]([S:32]([C:35]2[CH:36]=[CH:37][C:38]([CH3:39])=[CH:40][CH:41]=2)(=[O:34])=[O:33])[CH:22]=[CH:23][C:24]=1[C:25]([OH:27])=[O:26])[CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

An orange solution of (R)-tert-butyl 2-(3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)propyl)-1-tosyl-1H-pyrrole-3-carboxylate (504c, 5.85 g, 10.00 mmol) in DCM (15 mL) was treated with TFA (15 mL, 202 mmol) and heated at 40° C. for 2 h. The TFA and DCM was removed in vacuo affording (R)-2-(1-amino-3-(benzyloxy)propyl)-1-tosyl-1H-pyrrole-3-carboxylic acid compound with 2,2,2-trifluoroacetic acid (1:1) (724d) as a dark orange viscous oil which was used for the next step without purification. m/z (ESI, +ve) 429.2 (M+1)′.

Workup

customThe TFA and DCM was removed in vacuo

Sources & evidence

ORD record: ord-70ef5c521609405eb369373c3a0c734c
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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