Ammonia → Boc-D-phenylalanylproline (6-amidino-3-picolyl)amide

HRID 1282282Notes

Reaction equation

HRID 1282282 reaction equation
Cl.[NH2:2]O.N.[C:5]([C:7]1[N:12]=[CH:11][C:10]([CH2:13][NH:14][C:15](=[O:39])[C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:38])[C@@H:22]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:9][CH:8]=1)#[N:6]>C(O)C>[C:5]([C:7]1[N:12]=[CH:11][C:10]([CH2:13][NH:14][C:15](=[O:39])[C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:38])[C@@H:22]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:23][C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])=[CH:9][CH:8]=1)(=[NH:2])[NH2:6]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 443297Hydroxyamine hydrochlorideHCID 54405429Boc-D-phenylalanylproline (6-cyano-3-picolyl)amide

Product 1

HCID 54365296Boc-D-phenylalanylproline (6-amidino-3-picolyl)amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.15 g (16.5 mmol) of hydroxylamine hydrochloride were suspended in 5 ml of ethanol, 1.2 g of 25% strength ammonia solution were added, and the mixture was stirred for 10 min. After addition of 45 ml of ethanol, the precipitated salt was filtered off with suction and 3.14 g (6.6 mmol) of the above compound (stage c) were added to the solution. The hydroxyamidine compound separated out after a short time and, after stirring for 30 minutes, was filtered off with suction and washed with a little cold water and ethanol. The residue moist with ethanol was dissolved in 40 ml of ethanol and 8 ml of glacial acetic acid, 250 mg of 10% Pd/C were added and hydrogenation was carried out at about 50° C. After 5 hours, TLC (CH2Cl2/MeOH/50% strength acetic acid, 20/5/1) showed no detectable starting material.

Workup

  1. additionwere added to the solution
  2. customThe hydroxyamidine compound separated out after a short time
  3. stirringafter stirring for 30 minutes
  4. filtrationwas filtered off with suction
  5. washwashed with a little cold water and ethanol
  6. dissolutionThe residue moist with ethanol was dissolved in 40 ml of ethanol
  7. addition8 ml of glacial acetic acid, 250 mg of 10% Pd/C were added
  8. customwas carried out at about 50° C
  9. waitAfter 5 hours

Sources & evidence

ORD record
ord-235a5cef7f12495eb59cbce757ef345b
Source dataset
uspto-grants-2002_09
Patent number
US06455671B1

Reaction notes

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