Cyanamide → HCID 508619, compound

HRID 396909Notes

Reaction equation

HRID 396909 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][C@H:27]([N:31]([S:36]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH2:32][CH:33]([CH3:35])[CH3:34])[C:28]([OH:30])=[O:29])=S)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:46]#[C:47][NH2:48]>CO.[NH4+].[Cl-]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C@H:12]([C:20]([NH:48][C:47]#[N:46])=[N:22][CH2:23][CH2:24][CH2:25][CH2:26][C@H:27]([N:31]([S:36]([C:39]2[CH:40]=[CH:41][C:42]([CH3:45])=[CH:43][CH:44]=2)(=[O:37])=[O:38])[CH2:32][CH:33]([CH3:34])[CH3:35])[C:28]([OH:30])=[O:29])[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9864CyanamideHCID 3006319HCID 3006319, compound

Product 1

HCID 508619HCID 508619, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred solution of the thioamide, Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-Nε-[N′α-(4-methylbenzenesulfonyl)-L-thiophenylalanyl]-L-lysine, (227 mg, 0.33 mmol, example 72) 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 128 mg (57%) 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-0dd3aef57bd643b780a0f56b0841bf0a
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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