Cyanamide → HCID 508624, compound

HRID 397793Notes

Reaction equation

HRID 397793 reaction equation
CC1C=CC(S(N[C@H:12]([C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][C@H:30]([N:34]([S:39]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)(=[O:41])=[O:40])[CH2:35][CH:36]([CH3:38])[CH3:37])[C:31]([OH:33])=[O:32])=S)[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)(=O)=O)=CC=1.[N:49]#[C:50][NH2:51].[NH4+:52].[Cl-]>CO>[CH3:48][C:45]1[CH:46]=[CH:47][C:42]([S:39]([NH:52][C@H:12]([C:23]([NH:49][C:50]#[N:51])=[N:25][CH2:26][CH2:27][CH2:28][CH2:29][C@H:30]([N:34]([S:39]([C:42]2[CH:43]=[CH:44][C:45]([CH3:48])=[CH:46][CH:47]=2)(=[O:40])=[O:41])[CH2:35][CH:36]([CH3:37])[CH3:38])[C:31]([OH:33])=[O:32])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)(=[O:41])=[O:40])=[CH:43][CH:44]=1

Participants

5

Reactant 3

HCID 9864CyanamideHCID 25517Ammonium ChlorideHCID 3006320HCID 3006320, compound

Product 1

HCID 508624HCID 508624, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of thioamide Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-Nε-[N′α-(4-methylbenzenesulfonyl)-L-thiotryptophanyl]-L-lysine (240 mg, 0.33 mmol, example 73) in MeOH (3 mL) was added cyanamide (28 mg, 0.66 mmol). The mixture was stirred for 5 min, then mercuric acetate (209 mg, 0.66 mmol) was added. The reaction was stirred for 3 h then diluted with saturated NH4Cl and extracted with EtOAc. The organic layer was washed with brine and concentrated then rediluted with THF/MeOH (2 mL/1 mL) and treated with 1N NaOH (0.8 mL). After stirring for 4 h, the reaction was acidified with 1N HCl and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated and purified by column chromatography to give 154 mg (65%) of the final product.

Workup

  1. stirringThe reaction was stirred for 3 h
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated
  5. additionthen rediluted with THF/MeOH (2 mL/1 mL)
  6. additiontreated with 1N NaOH (0.8 mL)
  7. stirringAfter stirring for 4 h
  8. extractionextracted with EtOAc
  9. dry with materialThe organic layer was dried over MgSO4
  10. concentrationconcentrated
  11. custompurified by column chromatography

Sources & evidence

ORD record
ord-0e176c3b208542a0a922c57497796327
Source dataset
uspto-grants-2003_08
Patent number
US06610689B2

Reaction notes

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