Trifluoroacetic acid → HCID 131714516, compound

HRID 1589115Notes

Reaction equation

CC(C)(OC([NH:7][C@@H:8]([C:27](=[O:36])OCC1C=CC=CC=1)[CH2:9][CH2:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C@H:14]1[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:12])=O)C.[C:38]1(OC)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]>>[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49].[NH2:7][C@@H:8]([C:27](=[O:36])[CH2:47][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:9][CH2:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C@H:14]1[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:12]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid2×

HCID 7519Anisole

HCID 86740644HCID 86740644, compound

Product 1

HCID 131714516HCID 131714516, compound

Procedure

A mixture of the ester product from part (e) (0.39 mmole, 0.2 g.), anisole (0.2 ml.) and trifluoroacetic acid (1.95 ml.) is allowed to stir at room temperature for two hours. The trifluoroacetic acid is stripped in vacuo to yield (S)-1-[(R)-4-amino-1,5-dioxo-5-(phenylmethyl)-pentyl]-2,3-dihydro-1H-indole-2-carboxylic acid, ethyl ester, trifluoroacetate salt as a yellow oil.

Sources & evidence

ORD record: ord-0ecd1bf7988943a2809e4ca6d28068ca
Source dataset: uspto-grants-1986_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04568489

Reaction notes

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