Trifluoroacetic acid → HCID 20662229, compound

HRID 1067094Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11](=[O:47])[C@H:12]([CH2:33][CH2:34][CH2:35][NH:36]C(OCC1C=CC=CC=1)=O)[NH:13][C:14](=[O:32])[C@H:15]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:16]C(OC(C)(C)C)=O.[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51]>>[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11](=[O:47])[C@H:12]([CH2:33][CH2:34][CH2:35][NH2:36])[NH:13][C:14](=[O:32])[C@H:15]([CH2:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[NH2:16]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 88211846HCID 88211846, compound

Product 1

HCID 20662229HCID 20662229, compound

Procedure

A solution of Boc-homophenylalanyl-Nδ-Cbz-ornithinyl 2-benzothiazolyl thioether (B) (35 mg) and trifluoroacetic acid (10 ml) was kept at 25° C. for 2 hrs and concentrated in vacuo. After HPLC purification (method A, retention time=42.1 min), there was obtained a white solid (33 mg): 1H NMR (400 MHz, D2O) δ1.78-1.90 (m, 4H), 2.04 (m, 2H), 2.62 (m, 2H), 3.11 (m, 2H), 3.44 (dd, J=13.3; 9.6 Hz, 1H), 3.79 (dd, J=13.0; 2.7 Hz, 1H), 4.06 (t, J=5.9 Hz, 1H), 4.41 (m, 1H), 7.03 (m, 2H), 7.24 (m, 3H), 7.42 (t, J=8.5 Hz, 1H), 7.55 (t, J=9.4 Hz, 1H), 7.81 (d, J=9.5 Hz, 1H), and 7.85 (d, J=8.6 Hz, 1H).

Workup

concentrationconcentrated in vacuo
customAfter HPLC purification (method A, retention time=42.1 min)

Sources & evidence

ORD record: ord-59fb0be86ca8449c8f8f98eebbc392ec
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245746B1

Reaction notes

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