Diisopropylethylamine → HCID 59287698, compound

HRID 1776971Notes

Reaction equation

HRID 1776971 reaction equation
[C:1]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(C(C)C)CC)(C)C.[C:24](=O)([O:35]C1C=CC([N+]([O-])=O)=CC=1)[O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][N+:32]([O-:34])=[O:33]>C(Cl)Cl.[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[CH3:5][C:4]([CH3:7])([O:3][C:1](=[O:2])[NH:8][CH:9]([C:12]([OH:14])=[O:13])[CH2:10][O:11][C:24](=[O:35])[O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][N+:32]([O-:34])=[O:33])[CH3:6]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 86640999HCID 86640999, compound

Product 1

HCID 59287698HCID 59287698, compound

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Into a solution or N-Boc-L-Serine (1.66 g, 8.12 mmol), diisopropylethyl amine (DIPEA) (1.41 ml, 8.12 mmol), N,N-dimethylaminopyridine (DMAP) (1.19 g, 9.74 mmol) and scandium triflate (1.20 g, 2.43 mmol) in CH2Cl2 (40 ml), cooled to −10° C., a solution of 2-[2-(nitrooxy)ethoxy]ethyl 4-nitrophenyl carbonate in CH2Cl2 (40 ml) was added drop-wise. The reaction was slowly warmed to room temperature and stirred for 24 h. Then the organic phase was washed with pH 3 aqueous buffer and concentrated under reduced pressure. The crude was partitioned between aqueous 5% aqueous Na2HPO4 and diethyl ether and extracted twice with diethyl ether. The aqueous phase was acidified to pH 3 and extracted with CH2Cl2. The organic phase was finally dried over sodium sulphate and concentrated under reduced pressure to give the title compound as an oil. (2.4 g, 80%)

Workup

  1. washThen the organic phase was washed with pH 3 aqueous buffer
  2. concentrationconcentrated under reduced pressure
  3. customThe crude was partitioned between aqueous 5% aqueous Na2HPO4 and diethyl ether
  4. extractionextracted twice with diethyl ether
  5. extractionextracted with CH2Cl2
  6. dry with materialThe organic phase was finally dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cf912ced2bf344f2a0b72d8eca0942a3
Source dataset
uspto-grants-2016_02
Patent number
US09266820B2

Reaction notes

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