Tributylstannane → HCID 54548066, compound

HRID 582818Notes

Reaction equation

HRID 582818 reaction equation
[CH2:1]([O:8][C:9](=[O:31])[CH:10]([NH:19][C:20](=[O:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:11][CH2:12][C:13]([O:15]CC=C)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SnH](CCCC)CCCC)CCC>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:31])[CH:10]([NH:19][C:20](=[O:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 54256118HCID 54256118, compound

Product 1

HCID 54548066HCID 54548066, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pd(O)-catalyzed deprotection of the allyl ester proceeded as follows to yield 2-Decanoylamino-pentanedioic acid 1-benzyl ester (8). To a solution of 752 mg (1.74 mmol) of 2-decanoylamino-pentanedioic acid 7 in 10 mL of CH2Cl2 was added 100 mg (0.087 mmol) of tetrakistriphenylphosphine Pd(O) followed by 0.52 mL (1.9 mmol) of tributyltin hydride. After 15 min, the reaction mixture was quenched with 10 mL of a 10% HCl solution. The aqueous layer was reextracted with 15 mL of CH2Cl2 and the organic layer dried (Na2SO4), concentrated in vacuo, and chromatographed on SiO2 (Hexanes/EtOAc, 9:1) to provide 545 mg (79.9%) of 8 as a thick oil: [α]D +2.8° (c 1.2, CHCl3, 21° C.); IR (neat) 3351, 3064, 2995, 2852, 1738, 1712, 1657, 1536, 1454, 1380, 1364, 1265, 1209, 1183, 1121, 739 cm-1 ; 1H NMR δ 10.9-10.7 (bs, 1 H), 7.22 (s, 5 H), 6.58 (d, 1 H, J=7.8 Hz), 5.09 (s, 2 H), 4.63 (dd, 1 H, J=8.1, 12.9 Hz), 2.4-2.25 (m, 2 H), 2.2-2.1 (m, 3 H), 2.0-1.9 (m, 1 H), (m, 6 H), 1.53 (t, 2 H, J=6.6 Hz), 1.19 (bs, 12 H), 0.81 (t. 3 H, J=6.0 Hz); 13C NMR δ 176.9, 174.0, 171.8, 134.9, 128.5, 128.4, 128.1, 67.3, 51.4, 36.2, 31.7, 29.9, 29.3, 29.2, 29.1, 27.0, 25.5, 22.5, 14.0; MS (El) m/z (relative intensity) 391 (54), 373 (62), 279 (13), 256 (19), 178 (27), 178 (23), 155 (13), 146 (6), 130 (7), 102 (100); HRMS (El) m/z calculated for C22H33NO5 :391.2358, found: 391.2350.

Workup

  1. customthe reaction mixture was quenched with 10 mL of a 10% HCl solution
  2. dry with materialthe organic layer dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customchromatographed on SiO2 (Hexanes/EtOAc, 9:1)

Sources & evidence

ORD record
ord-9c3a6781964b4be3a86abbb4e51a8c06
Source dataset
uspto-grants-1999_07
Patent number
US05925660

Reaction notes

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