Sulfuric Acid → N-(Triphenylmethyl)-L-asparagine

HRID 618434노트

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HRID 618434 반응식
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[C:10](O)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.OS(O)(=O)=O.C(OC(=O)C)(=O)C.[OH-].[Na+]>C(O)(=O)C.O>[CH:26]1[CH:27]=[CH:28][C:23]([C:10]([NH:5][C:4]([CH2:3][C@H:2]([NH2:1])[C:7]([OH:9])=[O:8])=[O:6])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:24][CH:25]=1

참가 물질

8

반응물 5

HCID 1118Sulfuric AcidHCID 6267(-)-AsparagineHCID 6457TriphenylcarbinolHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide

생성물 1

HCID 7408309N-(Triphenylmethyl)-L-asparagine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

Bpoc-Asn(Trt)--OH: H-Asn(Trt)--OH was prepared according to the procedure of Sieber and Riniker (40) with the following modifications. H-Asn-OH (13.2 g, 0.1 mol), trityl alcohol (52 g, 0.2 mol), conc. H2SO4 (6.1 mL, 0.115 mol) were suspended in glacial acetic acid (300 mL) for 10 min. Acetic anhydride (9 mL, 0.2 mol) was added and the reaction was heated to 60° C. After 4 h the solution was slowly added to cold water (600 mL) and adjusted to pH 6 by addition of 10 N NaOH. After 1 h at 0° C., white crystals were collected and washed thoroughly with water and toluene. Drying under vacuum for 24 h yielded white crystals (36 g, 94%). mp>240 dec., lit. >240 dec.

후처리

  1. customwhite crystals were collected
  2. washwashed thoroughly with water and toluene
  3. customDrying under vacuum for 24 h

출처 및 근거

ORD 기록
ord-7c06b6ebc76f468689461bd9ee367f15
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952497

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