Decanoyl chloride → HCID 54256118, compound

HRID 582817Notes

Reaction equation

HRID 582817 reaction equation
[CH2:1]([O:8][C:9](=[O:37])[CH:10]([NH:19][C:20]([O:22]CC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38](Cl)(=O)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9](=[O:37])[CH:10]([NH:19][C:20](=[O:22])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 66982Decanoyl chlorideHCID 53676667HCID 53676667, compound

Product 1

HCID 54256118HCID 54256118, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

The Fmoc protective group was subsequently removed by exposure to DMAP and the free amine was acylated in situ with decanoyl chloride to give 2-Decanoylamino-pentanedioic acid 5-allyl ester 1-benzyl ester (7) in 63% yield as follows. To a suspension of 1 g (2.0 mmol) of 6 in 10 mL of CH2Cl2 was added 1 g (8.2 mmol) of DMAP. The reaction mixture was stirred at 22° C. for 24 h, treated with 0.62 mL (3.0 mmol) of decanoyl chloride, stirred for 2 h at 22° C., and extracted with saturated sodium bicarbonate solution (2×10 mL). The organic layer was dried (Na2SO4), evaporated to dryness, and the residue was chromatographed on SiO2 (Hexanes/EtOAc, 5:1) to give 548 mg (63%) of 7 as a viscous oil: IR (neat) 3293, 3063, 2924, 2855, 1740, 1649, 1534, 1453, 1379, 1175, 986, 930 cm-1 ; 1H NMR δ 7.26 (s, 5 H), 6.68 (d, I H, J=7.8 Hz), 5.85-5.75 (m, 1 H), 5.22 (d, 1 H, J=17.3 Hz), 5.14 (d, 1 H, J=10.4 Hz), 5.08 (s, 2 H), 4.63-4.57 (m, 1 H), 4.48 (d, 2 H, J=5.6 Hz), 2.38-2.28 (m, 2 H), 2.2-2.1 (m, 3 H), 2.0-1.9 (m, 1 H), 1.55 (t, 2 H, J=6.9 Hz), 1.20 (bs, 12 H), 0.82 (t, 3 H, J=5.9 Hz); 13C NMR δ 173.0, 172.1, 171.6, 135.0, 131.7, 128.2, 128.1, 127.8, 117.9, 66.8, 64.9, 51.3, 36.0, 31.6, 29.9, 29.1, 29.0, 26.8, 25.3, 22.3, 13.8; MS (El) m/z (relative intensity) 431 (12), 319 (21), 296 (51), 142 (100), 124 (31), 91 (91); HRMS (El) m/z calculated for C25H37NO5 : 431.2672, found: 431.2673.

Workup

  1. customThe Fmoc protective group was subsequently removed by exposure to DMAP
  2. customto give 2-Decanoylamino-pentanedioic acid 5-allyl ester 1-benzyl ester (7) in 63% yield
  3. stirringstirred for 2 h at 22° C.
  4. extractionextracted with saturated sodium bicarbonate solution (2×10 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated to dryness
  7. customthe residue was chromatographed on SiO2 (Hexanes/EtOAc, 5:1)

Sources & evidence

ORD record
ord-9a794136f2d04cccb5f0bfb51f82ead4
Source dataset
uspto-grants-1999_07
Patent number
US05925660

Reaction notes

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