Ammonia → N-t-Butoxycarbonyl-S-(2-aminoethyl)-L-cysteine

HRID 1981887ノート

反応式

HRID 1981887 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25]([OH:27])=[O:26])[CH2:10][S:11][CH2:12][CH2:13][NH:14]C(OCC1C=CC=CC=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].N.[Na].[Cl-].[NH4+].[NH4+]>O.C(O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25]([OH:27])=[O:26])[CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 5

HCID 222AmmoniaHCID 223AmmoniumHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 7408384Boc-cys(Z-aminoethyl)-OH

生成物 1

HCID 22946527N-t-Butoxycarbonyl-S-(2-aminoethyl)-L-cysteine収率 76.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

N-t-Butoxycarbonyl-S-(2-carbobenzoxyaminoethyl)-L-cysteine (9.9 g) in 500 ml of liquid ammonia is treated with sodium metal until reaction is complete, as indicated by the persistence of a blue color. Ammonium chloride (1 g) is added, followed by ethanol (50 ml). Excess ammonia is let evaporate away. The residue is dissolved in a minimal amount of water, and extracted with ether. The aqueous layer is again taken to dryness, and the residue extracted with ethanol containing 6 ml of ammonium hydroxide. Upon removal of the ethanol the residue obtained is redissolved in 15 ml of water, and passed through 10 ml of Dowex-50 resin on the ammonium cycle. The resin is washed with 30 ml of water. The product (5.0 g) is obtained upon lyophilization of the eluent. The NMR spectrum (in D2O and NaOD) of such a sample shows a multiplet at 4.1, complex absorption between 2.6 and 3.0, and a singlet at 1.4.

後処理

  1. customExcess ammonia is let evaporate away
  2. dissolutionThe residue is dissolved in a minimal amount of water
  3. extractionextracted with ether
  4. extractionthe residue extracted with ethanol containing 6 ml of ammonium hydroxide
  5. customUpon removal of the ethanol the residue
  6. customobtained
  7. washThe resin is washed with 30 ml of water

出典と根拠

ORDレコード
ord-3c509e3ba7124540a1111817fd2c9915
出典データセット
uspto-grants-1986_06
特許番号
US04594341

反応ノート

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