Ammonia → HCID 23318048, compound

HRID 1981895Notes

Reaction equation

HRID 1981895 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:28]([OH:30])=[O:29])[CH2:10][CH2:11][S:12][CH2:13][CH:14]([NH2:27])C(C(OCC1C=CC=CC=1)=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na].N>>[C:1]([O:5][C:6]([NH:8][CH:9]([C:28]([OH:30])=[O:29])[CH2:10][CH2:11][S:12][CH2:13][CH2:14][NH2:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 131714713HCID 131714713, compound

Product 1

HCID 23318048HCID 23318048, compound

Procedure

N-t-Butoxycarbonyl-S-(2-carbobenzyloxycarbonyl aminoethyl)-D,L-homocysteine (1.0 g) is treated with sodium in liquid ammonia according to the procedure described in Example 2. After the ammonia has evaporated off, the residue is extracted with ethanol. Inorganic salts (0.4 g) is removed by filtration. After removal of ethanol, the residue is taken up in 5 ml of water. The aqueous solution is extracted with ether, and then acidified to pH 4 with 4M hydrochloric acid. The solution is concentrated to a volume of 2 ml. Excess ether is added. The product crystallizes out as a white solid (0.32 g). The NMR spectrum (in MeOH-d4 and NaOD) shows a triplet at 3.7, complex absorption between 2.1 and 2.6, a multiplet between 1.5 and 1.9, and a singlet at 1.2.

Workup

  1. customAfter the ammonia has evaporated off
  2. extractionthe residue is extracted with ethanol
  3. customInorganic salts (0.4 g) is removed by filtration
  4. customAfter removal of ethanol
  5. extractionThe aqueous solution is extracted with ether
  6. concentrationThe solution is concentrated to a volume of 2 ml
  7. additionExcess ether is added
  8. customThe product crystallizes out as a white solid (0.32 g)
  9. customat 3.7, complex absorption between 2.1 and 2.6

Sources & evidence

ORD record
ord-81b6d9fd78824384b5b4e0fc5a019977
Source dataset
uspto-grants-1986_06
Patent number
US04594341

Reaction notes

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