2-Methyltetrahydrofuran → 5-Chloro-N-((S)-2,3-dihydroxypropyl)thiophene-2-carboxamide

HRID 425234Notes

Reaction equation

HRID 425234 reaction equation
C(=O)([O-])O.[Na+].Cl.[NH2:7][CH2:8][C@H:9]([OH:12])[CH2:10][OH:11].CC1CCCO1.[Cl:19][C:20]1[S:24][C:23]([C:25](Cl)=[O:26])=[CH:22][CH:21]=1>O.C1(C)C=CC=CC=1>[OH:12][C@H:9]([CH2:10][OH:11])[CH2:8][NH:7][C:25]([C:23]1[S:24][C:20]([Cl:19])=[CH:21][CH:22]=1)=[O:26]

Participants

7

Reactant 4

HCID 73012-MethyltetrahydrofuranHCID 516892Sodium BicarbonateHCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 53487907(S)-3-Amino-1,2-dihydroxypropane hydrochloride

Product 1

HCID 99916905-Chloro-N-((S)-2,3-dihydroxypropyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
16.5 °C

Procedure

461 g of sodium hydrogencarbonate and 350 g of (2S)-3-aminopropane-1,2-diol hydrochloride (VII) (commercially available) are initially charged at from 13 to 15° C. in 2.1 l of water and admixed with 950 ml of 2-methyltetrahydrofuran. 535.3 g of 5-chlorothiophene-2-carbonyl chloride (approx. 93%) in 180 ml of toluene are added dropwise to this mixture with cooling at from 15 to 18° C. over a period of two hours. For workup, the phases are separated and the organic phase is admixed in several steps with a total of 1.5 l of toluene. The precipitated product is filtered off with suction, washed with ethyl acetate and dried.

Workup

  1. customFor workup, the phases are separated
  2. filtrationThe precipitated product is filtered off with suction
  3. washwashed with ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-b081fb1c16d84c258f9132468a2866a9
Source dataset
uspto-grants-2012_01
Patent number
US08106192B2

Reaction notes

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