4-Fluorobenzenehexanamine → HCID 54269383, compound

HRID 1603662Notes

Reaction equation

HRID 1603662 reaction equation
[CH2:1]([S:8][C@H:9]1[N:12]([CH2:13][C:14]([OH:16])=O)[C:11](=[O:17])[C@@H:10]1[Cl:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH2:32])=[CH:22][CH:21]=1>>[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:14](=[O:16])[CH2:13][N:12]2[C@H:9]([S:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@@H:10]([Cl:18])[C:11]2=[O:17])=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 184704154-FluorobenzenehexanamineHCID 57285357HCID 57285357, compound

Product 1

HCID 54269383HCID 54269383, compoundYield 85%

Procedure

Treatment of (3S,4R)-(4-benzylthio-3-chloro-2-oxoazetidin-1-yl)acetic acid with 6-(4-fluorophenyl)hexylamine under the conditions described for Example 86 gave the title compound as a colourless oil, 85% yield. 1H NMR δ (CDCl3) 1.3-1.6 (8H, m, 4xCH2), 2.56 (2H, t, J=7.6 Hz, CH2Ph), 3.22 (2H, m, NHCH2), 3.51, 3.81 (each 1H, d, J=16.5 Hz, NCH2), 3.83 (2H, s, SCH2), 4.58 (1H, d, J=1.7 Hz, H4), 4.79 (1H, d, J=1.7 Hz, H3), 5.80 (1H, m, NH), 6.95 (2H, m, 4-FPh--H), (2H, m, 4-FPh--H), 7.30 (5H, m. Ph--H)

Sources & evidence

ORD record
ord-04045e92d7eb4b6f82fa56df8316f211
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

Loading…