D-Cysteine → HCID 69602147, compound

HRID 1911947Notes

Reaction equation

HRID 1911947 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][C:6]([C:7]#[N:8])=[C:5](O)[CH:4]=1.N[C@@H:15]([C:18]([OH:20])=[O:19])[CH2:16][SH:17].C(=O)(O)[O-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][C:6]([C@H:7]2[NH:8][C:15]([C:18]([OH:20])=[O:19])=[CH:16][S:17]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 92851D-CysteineHCID 516892Sodium BicarbonateHCID 14388660HCID 14388660, compound

Product 1

HCID 69602147HCID 69602147, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-2-(4′,5′-dimethoxyphenyl)-4-thiazoline-4-carboxylic acid (1) and (S)-2-(4′,5′-dimethoxyphenyl)-4-methylthiazoline-4-carboxylic acid (2) (also referred to as (S)-4′,5′-dimethoxydesazadesmethyldesferrithiocin and (S)-4′,5′-dimethoxydesazadesferrithiocin, respectively) were prepared starting with 2-benzyloxy-4,5-dimethoxybenzaldehyde (6), which was converted to the corresponding oxime by reacting 6 with hydroxylamine hydrochloride and triethylamine in acetonitrile at about 50° C. for about 18 hours. The corresponding nitrile (7) was prepared from the oxime by refluxing the intermediate product with phthalic anhydride for 1 day to give nitrile 7 in 87% yield. Nitrile 7 was reacted with hydrogen on a Pd—C catalyst in an ethanol/ethyl acetate mixture for about 50 minutes to remove the O-benzyl group and form 4,5-dimethoxy-2-hydroxybenzonitrile (8) in 84% yield. The deprotected nitrile 8 was subsequently reacted with D-cysteine or D-alpha-methylcysteine in a pH 6 buffer containing sodium bicarbonate and methanol to form products 1 and 2, respectively.

Sources & evidence

ORD record
ord-938b3cadbb3e40bdac4e9d75114f1cea
Source dataset
uspto-grants-2013_12
Patent number
US08604216B2

Reaction notes

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