Hydrochloric Acid → 1-tert-Butyl 18-(2,5-dioxopyrrolidin-1-yl) octadecanedioate

HRID 2169110노트

반응식

HRID 2169110 반응식
[C:1]([O:5][C:6](=[O:26])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(O[N:40]1[C:45](=[O:46])[CH2:44][CH2:43][C:41]1=[O:42])=[N+](C)C)C.CCN(C(C)C)C(C)C.Cl>C1COCC1.C(#N)C>[O:42]=[C:41]1[CH2:43][CH2:44][C:45](=[O:46])[N:40]1[O:24][C:23](=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:26]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 2728247318-(Tert-butoxy)-18-oxooctadecanoic acid

생성물 1

HCID 582492131-tert-Butyl 18-(2,5-dioxopyrrolidin-1-yl) octadecanedioate

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

실험 절차

Octadecanedioic acid mono-tert-butyl ester (4.2 g, 0.011 mol) was dissolved in THF (20 mL), TSTU (4 g, 0.013 mol) in acetonitrile (20 mL) was added and pH of the solution was adjusted to 8 with dropwise addition of DIPEA. The mixture was stirred at RT for 4 h, then acidified with HCl (2M) to pH 3 and evaporated in vacuo. The residual oil was subsequently partitioned between ethyl acetate and HCl (0.1 M). The organic layer was dried (MgSO4), filtered and evaporated to dryness in vacuo. This afforded 5.2 g of octadecanedioic acid tert-butyl ester 2,5-dioxopyrrolidin-1-yl ester as an oil, which could be used in the next step without further purification. LC-MS (electrospray): m/z=468 (M+1) and 412 (M+1-tBu).

후처리

  1. customevaporated in vacuo
  2. customThe residual oil was subsequently partitioned between ethyl acetate and HCl (0.1 M)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. customThis afforded 5.2 g of octadecanedioic acid tert-butyl ester 2,5-dioxopyrrolidin-1-yl ester as an oil, which could be used in the next step without further purification

출처 및 근거

ORD 기록
ord-24435b4a52ee480f8041c06c932f1dba
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045560B2

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