Boc-D-Phenylalanyl-Ndelta-CBz-Ornithinyl 2-Benzothiazolyl Thioether → D-Phenylalanyl-Ornithinyl 2-Benzothiazolyl Thioether Trifluoroacetate

HRID 1067095Notes

Reaction equation

HRID 1067095 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:46])[C@H:12]([CH2:32][CH2:33][CH2:34][NH:35]C(OCC1C=CC=CC=1)=O)[NH:13][C:14](=[O:31])[C@@H:15]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH:16]C(OC(C)(C)C)=O.[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50].C([SiH](CC)CC)C>>[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50].[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:46])[C@H:12]([CH2:32][CH2:33][CH2:34][NH2:35])[NH:13][C:14](=[O:31])[C@@H:15]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[NH2:16]

Participants

3

Reactant 2

HCID 88211861Boc-D-Phenylalanyl-Ndelta-CBz-Ornithinyl 2-Benzothiazolyl ThioetherHCID 131722655TFA triethylsilane

Product 1

HCID 20662223D-Phenylalanyl-Ornithinyl 2-Benzothiazolyl Thioether Trifluoroacetate

Procedure

Boc-D-phenylalanyl-Nδ-CBz-ornithinyl 2-benzothiazolyl thioether (A) was stirred at 25° C. with trifluoroacetic acid-triethylsilane (3:1-10 ml) for 2 hrs and concentrated in vacuo. The crude residue was purified by HPLC.(method C, retention time=49.57 min); 1H NMR (400 MHz, D2O) δ1.46 (m, 3H), 1.74 (m, 1H), 2.98 (m, 2H), 3.22 (m, 2H), 3.40 (dd, J=13.6; 8.0 Hz, 1H), 3.66 (d, J=14.0 Hz, 1H), 4.17 (m, 2H), 7.30 (m, 2H), 7.44 (m, 3H), 7.52 (t, J=8.0 Hz, 1H), 7.62 (t, J=7.2 Hz, 1H), 7.94 (d, J=8.4 Hz, 1H), and 8.02 (d, J=8.4 Hz, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude residue was purified by HPLC.(method C, retention time=49.57 min)

Sources & evidence

ORD record
ord-27ccfdda4b964502ac72189b448a91d7
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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