Hydroxylamine → Dl-Phenylalanine

HRID 9932

반응식

HRID 9932 반응식
[C-]#N.NO.OC[C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](N)=O.C[C:17]([NH:19]CCCCCCNC(C)=O)=O.C1CCC(N=C=NC2CCCCC2)CC1.N1CCCCC1.CN([CH:54]=[O:55])C.C[O:57]C1C=CC(S(Cl)(=O)=O)=CC=1>>[NH2:19][CH:17]([C:54]([OH:55])=[O:57])[CH2:9][C:8]1[CH:7]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

8

반응물 7

HCID 787HydroxylamineHCID 3616Hexamethylene BisacetamideHCID 5975CyanideHCID 74014-Methoxybenzenesulfonyl chlorideHCID 10868DicyclohexylcarbodiimideHCID 99176o-(Hydroxymethyl)benzamideHCID 23501187piperidine N,N-dimethylformamide

생성물 1

HCID 994Dl-Phenylalanine

실험 절차

To explore the effectiveness of cyanide in the assistance of hydroxylamine mediated cleavage for solid phase library synthesis, hydroxymethylbenzamide (HMBA-AM) resin was chosen for the well-established compatibility between the ester linkage and Fmoc- and Boc-chemistry, and its stability towards Mitsunobu and reductive amination conditions. A solid phase library of DL-phenylalanine and several constrained analogs (AAa–c, Scheme 3) was prepared on the HMBA resin by the esterification of the Fmoc protected DL-aminoacids using standard DCC coupling conditions at room temperature overnight. The resin-bound Fmoc aminoacids BBa–c were deprotected with piperidine-DMF (1:4) and sulfonated with 4-methoxybenzenesulfonyl chloride to give Compounds IIIa–c. In this instance, the optimal reaction conditions for cleavage from the resin of the sulfonamide esters to yield the free hydroxamic acids (IVa–c, Table 2) were 5:5:2 THF:MeOH:50% aqueous NH2OH and 5 mg (0.08 mmol, 40 to 80 mol %) of KCN for 100 to 200 mg of loaded resin.

후처리

  1. customat room temperature
  2. customovernight
  3. customto give Compounds IIIa–c

출처 및 근거

ORD 기록
ord-a8694885db9e4896bdea2997d3fc339d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091378B2

연결된 노트

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