Diisopropylethylamine → tert-butyl (2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-ylcarbamate

HRID 1036683노트

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HRID 1036683 반응식
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.CCN(C(C)C)C(C)C.[CH3:49][N:50]1[CH2:54][C@H:53]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C@:52]2([CH2:65][CH2:64][CH2:63][NH:62][CH2:61]2)[C:51]1=[O:66].CN1C[C@@H](C2C=CC=CC=2)[C@@]2(CCCNC2)C1=O>CC#N.Cl>[CH2:1]([O:8][CH2:9][C@@H:10]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:11]([N:62]1[CH2:63][CH2:64][CH2:65][C:52]2([C:51](=[O:66])[N:50]([CH3:49])[CH2:54][CH:53]2[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH2:61]1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 2733693(R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acidHCID 71060185(4S,5R)-2-Methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one2회HCID 71060283(4R,5S)-2-Methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one

생성물 1

HCID 86674095tert-butyl (2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-ylcarbamate

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6342Acetonitrile용매

실험 절차

A mixture comprising (R)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoic acid (Sigma-Aldrich) (1.052 g, 3.56 mmol) and ®T3P (50% in EtOAc) (4.16 ml, 7.12 mmol) in MeCN (20 mL) was treated dropwise with DIPEA (2.488 ml, 14.25 mmol). The resulting solution was stirred at room temperature for 30 minutes, then a racemic mixture of (4R,5S)-2-Methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one and (4S,5R)-2-Methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one (Intermediate 1A) (1 g, 3.56 mmol) was added portionwise. The reaction mixture was stirred for 20 hours at room temperature. The reaction mixture was diluted with 0.1M HCl (20 mL) and extracted with DCM (20 mL). The aqueous phase was further extracted with DCM (3×20 mL). The combined organic portions were washed with a saturated solution of sodium bicarbonate (20 mL), water (20 mL), dried (MgSO4), and concentrated in vacuo to afford the title compound. No purification was performed on the title compound.

후처리

  1. additionwas added portionwise
  2. stirringThe reaction mixture was stirred for 20 hours at room temperature
  3. extractionextracted with DCM (20 mL)
  4. extractionThe aqueous phase was further extracted with DCM (3×20 mL)
  5. washThe combined organic portions were washed with a saturated solution of sodium bicarbonate (20 mL), water (20 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d8eb3aa6e5384a1a892868ecf4447f40
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546416B2

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