Ammonia → Z-Lys(boc)-NH2

HRID 1732520Notes

Reaction equation

HRID 1732520 reaction equation
[NH3:1].[CH3:2][C:3]([O:6][C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C:15](OC1C=CC([N+]([O-])=O)=CC=1)=[O:16])=[O:8])([CH3:5])[CH3:4]>C1COCC1>[CH2:31]([O:30][C:28]([NH:27][C@H:14]([C:15]([NH2:1])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:7]([O:6][C:3]([CH3:5])([CH3:4])[CH3:2])=[O:8])=[O:29])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 135032652212-69-3

Product 1

HCID 10619711Z-Lys(boc)-NH2

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stream of NH3 was passed over a solution of Z-Lys(Boc)ONp (10.2 g, 2.0 mmole, Bachem) in THF (200 ml) for about 3 hr. A precipitate formed. The solvent was removed and the residue triturated and thoroughly washed with ether. The dried protected amide weighed 5.8 g (75%), m.p. 140°-142°, [α]D24 +1.9° (c 1.3. DMF): RfB, 0.54; RfG, 0.54.

Workup

  1. customA precipitate formed
  2. customThe solvent was removed
  3. customthe residue triturated
  4. washthoroughly washed with ether

Sources & evidence

ORD record
ord-3bff40df1a6147d9a3b3cd10610632a7
Source dataset
uspto-grants-1980_12
Patent number
US04237046

Reaction notes

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