Triethylamine → 2-(N-Allyloxycarbonylglycylamino)-Ethanethiol

HRID 1903174Notes

Reaction equation

HRID 1903174 reaction equation
C(Cl)(=O)C(C)(C)C.[CH2:8]([O:11][C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])[CH:9]=[CH2:10].C(N(CC)CC)C.Cl.[NH2:27][CH2:28][CH2:29][SH:30]>C(Cl)Cl.C(O)C>[CH2:8]([O:11][C:12]([NH:14][CH2:15][C:16]([NH:27][CH2:28][CH2:29][SH:30])=[O:18])=[O:13])[CH:9]=[CH2:10]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 9082Cysteamine HydrochlorideHCID 62493Pivaloyl chlorideHCID 11964402N-[(allyloxy)carbonyl]glycine

Product 1

HCID 132983102-(N-Allyloxycarbonylglycylamino)-Ethanethiol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

Add pivaloyl chloride (2.4 ml) in CH2Cl2 (10 ml) to a cooled (0°-5° C.) and stirred solution of N-allyloxycarbonylglycine (3.18 g) and triethylamine (2.8 ml) in dry CH2Cl2 (50 ml). Stir the mixture at 0°-5° C. for 15 mins. and then add a solution of 2-aminoethanethiol hydrochloride (2.4 g) and triethylamine (2.8 ml) in ethanol (15 ml) and CH2Cl2 (40 ml). Stir at room temperature for 1 hour, wash the mixture with aqueous 2 N-H2SO4 and aqueous NaHCO3, dry and evaporate. Triturate the resulting solid with ether, filter and dry to give the title compound.

Workup

  1. temperaturea cooled (0°-5° C.)
  2. stirringStir at room temperature for 1 hour
  3. washwash the mixture with aqueous 2 N-H2SO4 and aqueous NaHCO3
  4. customdry
  5. customevaporate
  6. customTriturate the resulting solid with ether
  7. filtrationfilter
  8. customdry

Sources & evidence

ORD record
ord-125af112d4bf4ca4942cd3b86fb1c26e
Source dataset
uspto-grants-1984_03
Patent number
US04435413

Reaction notes

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