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Dimethyl Sulfoxide → tert-Butyl amino(oxo)acetate

HRID 2181062
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HRID 2181062 반응식
CS(C)=O.[C:5](Cl)(=[O:9])[C:6](Cl)=[O:7].C(Cl)Cl.C(NO)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O.C([N:25](CC)CC)C>C(Cl)Cl.C1COCC1>[C:6]([C:5]([NH2:25])=[O:9])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 97534tert-butyl N-hydroxycarbamate

생성물 1

HCID 12453830tert-Butyl amino(oxo)acetate수율 85%

시약·촉매·용매 1

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트
HCID 21919333
Tetrahydrofurane dichloromethane
용매

실험 절차

DMSO (6.3 mL, 88 mmol) was added dropwise to a 2M solution of oxalyl chloride in CH2Cl2 (24.3 mL, 48.6 mmol) at −78° C. After 15 min, amino alcohol 22a (9.6 g, 44 mmol) in 80 mL CH2Cl2/THF (1:1) was added dropwise followed by dropwise addition of triethylamine (30.8 mL, 220 mmol) The reaction mixture was warmed to rt and stirred for 2. The reaction mixture was partitioned between EtOAc and sat KH2PO4, separated, and the organic layer was washed with brine, dried over MgSO4, filtered, and concentrated by rotary evaporator. The residue was purified by silica gel chromatography to give 8.0 g (85% yield) of Boc-amino ketone 22b.

후처리

  1. customThe reaction mixture was partitioned between EtOAc
  2. customseparated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporator
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-bbaba7ea071f4da7a65695a523f19ca2
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06890915B2

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