1-[(Chloroacetyl)oxy]pyrrolidine-2,5-dione → HCID 178520801, compound

HRID 1695606Notes

Reaction equation

HRID 1695606 reaction equation
[C@H:1]1([NH:11][C:12]2[O:13][CH2:14][C:15]3[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][C:16]=3[N:17]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.O=C1CCC(=O)N1[O:30][C:31](=O)[CH2:32][Cl:33]>C(#N)C>[Cl:33][CH2:32][C:31]([NH:22][C:20]1[CH:19]=[CH:18][C:16]2[N:17]=[C:12]([NH:11][C@H:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH2:4][CH2:3][CH2:2]3)[O:13][CH2:14][C:15]=2[CH:21]=1)=[O:30]

Participants

4

Reactant 2

HCID 125353371-[(Chloroacetyl)oxy]pyrrolidine-2,5-dioneHCID 178507255HCID 178507255, compound

Product 1

HCID 178520801HCID 178520801, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of (R)-N2-(1,2,3,4-tetrahydro-naphthalen-1-yl)-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 33) (293 mg, 1 mmol) and chloro-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester (CAS 27243-15-8) (192 mg, 1 mmol) in acetonitrile (2 ml) was stirred at 23° C. for 1 h. Poured onto water and extracted with ethyl acetate, dried the combined organic layers over sodium sulfate, filtered off and evaporated totally to give the title compound as a light red oil (370 mg, 100%, HPLC 1.185 min), MS (ISP) m/e=370.1 [(M+H)+] and 372 [(M+2+H)+].

Workup

  1. additionPoured onto water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried the combined organic layers over sodium sulfate
  4. filtrationfiltered off
  5. customevaporated totally

Sources & evidence

ORD record
ord-de339d558ace49058fcc9a381bf8a217
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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