Triethylamine → [3-Chloro-5-(tert-butyldimethylsilyloxy)phenyl]-n-cyclopentyl-n-prop-2-enylcarboxamide

HRID 988088Notes

Reaction equation

HRID 988088 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:10]=1)[C:5]([OH:7])=O.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[CH2:41]([NH:44][CH:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1)[CH:42]=[CH2:43]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([N:44]([CH:45]2[CH2:49][CH2:48][CH2:47][CH2:46]2)[CH2:41][CH:42]=[CH2:43])=[O:7])[CH:8]=[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 5062349N-(prop-2-en-1-yl)cyclopentanamineHCID 180074783-Chloro-5-(tert-butyldimethylsilyloxy)benzoic acid

Product 1

HCID 131724100[3-Chloro-5-(tert-butyldimethylsilyloxy)phenyl]-n-cyclopentyl-n-prop-2-enylcarboxamideYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-5-(tert-butyldimethylsilyloxy)benzoic acid (17.5 g, 60 mmol), as prepared in the preceding step, and CH2Cl2 (250 mL) were added triethylamine (33.8 mL, 0.24 mol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (17.0 g, 66 mmol). The resulting mixture was stirred for 5 min, then N-allylcyclopentylamine (9.8 mL, 66 mmol) was added. After 1 h, the solution was filtered. The filtrate was washed with 10% aqueous HCl (100 mL), saturated aqueous NaHCO3 (100 mL), and brine (100 mL). The organic layer was dried over anhydrous MgSO4, concentrated in vacuo, and flash chromatographed to provide the title compound as a colorless oil (23.5 g, 97%). 1H NMR (CDCl3) δ 6.95 (s, 1H), 6.84 (s, 1H), 6.71 (s, 1H), 5.93 (br s, 1H), 5.16 (d, 2H), 3.95 (br s, 3H), 1.4-1.9 (m, 8H), 0.97 (s, 9H), 0.20 (s, 6H). Mass spectrum (CI) calcd. for C21H32NO2SiCl: 394 (M+H). Found: 394.

Workup

  1. waitAfter 1 h
  2. filtrationthe solution was filtered
  3. washThe filtrate was washed with 10% aqueous HCl (100 mL), saturated aqueous NaHCO3 (100 mL), and brine (100 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo, and flash
  6. customchromatographed

Sources & evidence

ORD record
ord-63838f7432fe4393adea5a50beefd3b1
Source dataset
uspto-grants-2003_10
Patent number
US06635637B2

Reaction notes

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