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

HRID 2361850Notes

Reaction equation

HRID 2361850 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fc56045d271a437093c7af526f0f86b2
Source dataset
uspto-grants-2014_04
Patent number
US08691759B2

Reaction notes

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