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

HRID 1981887노트

반응식

HRID 1981887 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3c509e3ba7124540a1111817fd2c9915
출처 데이터셋
uspto-grants-1986_06
특허 번호
US04594341

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