2-Thiophenecarboxaldehyde → HCID 86601760, compound

HRID 1162549Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.Cl.[C:9]([O:13][C:14](=[O:18])[CH2:15][CH2:16][NH2:17])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([N:50]=[C:51]=[S:52])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.C(NCC)C>>[C:9]([O:13][C:14](=[O:18])[CH2:15][CH2:16][N:17]([CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:51]([NH2:50])=[S:52])([CH3:12])([CH3:11])[CH3:10]

Participants

Reactant 5

HCID 73642-Thiophenecarboxaldehyde

HCID 8021Diethylamine

HCID 4154759Fmoc isothiocyanate

HCID 5049666Sodium triacetoxyborohydride

HCID 16218890Tert-butyl 3-aminopropanoate hydrochloride

Product 1

HCID 86601760HCID 86601760, compound

Procedure

3-(1-Thiophen-2-ylmethyl-thioureido)-propionic acid tert-butyl ester was prepared (750 mg) following general procedure D using thiophene-2-carbaldehyde (0.466 mL, 5 mmol), beta-alanine tert-butyl ester hydrochloride (905 mg, 5 mmol), sodium triacetoxyborohydride (1.27 g, 6 mmol), Fmoc isothiocyanate (1.4 g, 95.3%, 5 mmol), and diethyl amine (2 mL). LCMS m/z: 301 (M+1)+.

Sources & evidence

ORD record: ord-5def32bf0c67453a8756b3594da9a097
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820704B2

Reaction notes

Loading…