Trifluoroacetic acid → HCID 21970626, compound

HRID 1067069Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:45])[C@H:12]([CH2:34][CH2:35][CH2:36][NH:37]C(OC(C)(C)C)=O)[N:13]([C:15](=[O:33])[C@H:16]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([I:32])=[CH:28][CH:27]=2)[NH:17]C(OC(C)(C)C)=O)[CH3:14])=[CH:4][CH:3]=1.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]>>[OH:50][C:48]([C:47]([F:52])([F:51])[F:46])=[O:49].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:45])[C@H:12]([CH2:34][CH2:35][CH2:36][NH2:37])[N:13]([C:15](=[O:33])[C@H:16]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([I:32])=[CH:30][CH:31]=2)[NH2:17])[CH3:14])=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 131722644HCID 131722644, compound

Product 1

HCID 21970626HCID 21970626, compound

Procedure

Boc-4-iodophenylalanyl-Nδ-Boc-Nα-methylornithine 2-(4-fluorophenyl)ethylamide was deprotected with trifluoroacetic acid (Procedure E) to afford a white solid: 1H NMR (400 MHz, D2O) δ1.50 (m, 1H), 1.60 (m, 1H), 1.71 (m, 1H), 1.83 (m, 1H), 2.73 (s, 2H), 2.92 (m, 2H), 3.03 (m, 3H), 3.12 (m, 1H), 3.59 (m, 2H), 4.74 (m, 1H), 4.91 (m, 1H), 7.04 (d, J=8.0 Hz, 1H), 7.11 (t, J=10.9 Hz, 2H), 7.35 (m, 2H), and 7.79 (d, J=8.5 Hz, 2H).

Workup

customto afford a white solid

Sources & evidence

ORD record: ord-26f5fda76122403a9f354965d01fd8f2
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245746B1

Reaction notes

Loading…