3-Benzyloxy-1-propanol → HCID 58880102, compound

HRID 1642589Notes

Reaction equation

HRID 1642589 reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[C:9]2[C:5]([C:6]3[CH:15]=[C:14]([CH3:16])[CH:13]=[N:12][C:7]=3[NH:8]2)=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH2:26][CH3:27])(=[O:25])=[O:24])[CH:18]=2)[CH:3]=1.[CH2:28]([O:35]CCCO)[C:29]1C=CC=C[CH:30]=1>[Pd].[H][H]>[Cl:1][C:2]1[C:10]([O:11][CH2:30][CH2:29][CH2:28][OH:35])=[C:9]2[C:5]([C:6]3[CH:15]=[C:14]([CH3:16])[CH:13]=[N:12][C:7]=3[NH:8]2)=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH2:26][CH3:27])(=[O:24])=[O:25])[CH:18]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 3479713-Benzyloxy-1-propanolHCID 58880184HCID 58880184, compound

Product 1

HCID 58880102HCID 58880102, compound

Reagents, catalysts & solvents 1

HCID 178506449HCID 178506449, compoundCatalyst

Procedure

The title compound was synthesized from Compound 247 and 3-(benzyloxy)propan-1-ol using an analogous procedure to that outlined in the preparation of Compound 210 followed by debenzylation using Pd/C—H2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16 (t, J=7.33 Hz, 3 H) 1.99-2.06 (m, 2 H) 2.25 (s, 3 H) 3.41 (q, J=7.58 Hz, 2 H) 3.71 (br. s., 2 H) 4.26 (t, J=6.44 Hz, 2 H) 4.81 (br. s., 1 H) 7.23 (s, 1 H) 7.46 (s, 1 H) 7.87 (t, J=7.71 Hz, 1 H) 8.03 (t, J=7,20 Hz, 2 H) 8.11 (s, 1 H) 8.31 (s, 1 H) 12.27 (br. s., 1 H); [M+H] calc'd for C23H24ClN2O4S, 459.1; found, 459.3.

Sources & evidence

ORD record
ord-d16101e1c5734499bb0672940074291b
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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