Water → HCID 9860587, compound

HRID 276975Notes

Reaction equation

HRID 276975 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.Cl.[CH2:13]([O:15][C:16](=[O:21])[C@H:17]([CH2:19][SH:20])[NH2:18])[CH3:14].C(N(C(C)C)C(C)C)C.O>C(O)C>[OH:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]2[NH:18][CH:17]([C:16]([O:15][CH2:13][CH3:14])=[O:21])[CH2:19][S:20]2)=[CH:4][C:5]=1[O:6][CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 81531DiisopropylethylamineHCID 2723617Ethyl cysteinate hydrochloride

Product 1

HCID 9860587HCID 9860587, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 1.52 g (10 mM) of vanillin (4-hydroxy-3-methoxybenzaldehyde) in 20 mL of absolute ethanol was added a solution of 1.85 g (10 mM) L-cysteine ethyl ester hydrochloride in 15 mL absolute ethanol, containing 1.7 mL (10 mM) of N-ethyldiisopropylamine. The reaction mixture was stirred at room temperature for about six hrs, until no starting material was present when monitored by thin layer chromatography (TLC). After adding 200 mL of water with stirring, the white precipitate was filtered, washed with 2×50 mL water, and vacuum dried. Yield 1.9 g (67%) of 1. 1H NMR (DMSO-d6; ˜1:1 diastereoisomeric mixture at C2)δ (1.22 m, 3H); (3.01 m and 3.15 m, 1H); (3.33 m, 2H); (3.75 s and 3.77 s, 3H); (4.15 m, and 4.38 bs, 2H); (5.40 d and 5.49 d, 1H); 6.79-6.73 m, 2H); 6.83-6.89 m 1H); (7.02 d and 7.12d, 1H); (8.99 s and 9.05 s, 1H). Mass analysis: Calculated for C13H17NO4S:284 [M+H]+. Found: 284.

Workup

  1. stirringwith stirring
  2. filtrationthe white precipitate was filtered
  3. washwashed with 2×50 mL water, and vacuum
  4. customdried
  5. custom1H NMR (DMSO-d6; ˜1:1 diastereoisomeric mixture at C2)δ (1.22 m, 3H); (3.01 m and 3.15 m, 1H); (3.33 m, 2H); (3.75 s and 3.77 s, 3H); (4.15 m, and 4.38 bs, 2H); (5.40 d and 5.49 d, 1H); 6.79-6.73 m, 2H)
  6. custom(7.02 d and 7.12d, 1H)
  7. custom(8.99 s and 9.05 s, 1H)

Sources & evidence

ORD record
ord-a3d0859a7b43412c9c77d49bf177ff59
Source dataset
uspto-grants-2002_03
Patent number
US06355661B1

Reaction notes

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