Hydrochloric Acid → 3-[4-(tert-Butyldiphenylsilanyloxy)-2-cyclohexylcarbamoyloxymethylphenyl]propionic acid tert-butyl ester

HRID 1181115Notes

Reaction equation

HRID 1181115 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:33][OH:34])([CH3:4])([CH3:3])[CH3:2].[CH:36]1([N:42]=[C:43]=[O:44])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.Cl.CCOCC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:11][C:10]=1[CH2:33][O:34][C:43](=[O:44])[NH:42][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 18502Cyclohexyl isocyanateHCID 589792063-[4-(tert-Butyldiphenylsilanyloxy)-2-hydroxymethylphenyl]propionic acid tert-butyl ester

Product 1

HCID 589793663-[4-(tert-Butyldiphenylsilanyloxy)-2-cyclohexylcarbamoyloxymethylphenyl]propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 100 mL round bottomed flask under N2 were charged with 3-[4-(tert-butyldiphenylsilanyloxy)-2-hydroxymethylphenyl]propionic acid tert-butyl ester (3.0 g, 6.11 mmol), cyclohexylisocyanate (4.7 mL, 36.7 mmol), and anhydrous CH2Cl2 (25 mL). A 1.0 M HCl solution in ether (3.06 mL, 3.06 mmol) was added, and the reaction mixture was stirred at ambient temperature under a nitrogen atmosphere for 16 h. The mixture was diluted with CH2Cl2 (100 mL), washed with brine, dried (Na2SO4), and concentrated to a brown oil. This crude oil was purified using the Biotage medium pressure chromatography system (EtOAc:hexanes 5:95) to a colorless oil (3.1 g, 82%). 1H NMR (400 MHz, CDCl3) 1.08-1.24 (m, 1H), 1.26-1.40 (m, 11H), 1.56-1.62 (m, 2H), 1.68-1.72 (m, 2H), 2.41 (t, J=8.3 Hz, 2H), 2.80 (t, J=7.8 Hz, 2H), 3.47 (br s, 1H), 4.56 (br s, 1H), 4.95 (s, 2H), 6.57 (dd, J=8.3, 2.7 Hz, 1H), 6.80 (s, 1H), 6.87 (d, J=8.6 Hz, 1H), 7.33-7.44 (m, 6H), 7.69-7.72 (m, 4H). MS (ES) m/e 616 (M+1).

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to a brown oil
  4. customThis crude oil was purified

Sources & evidence

ORD record
ord-6f0fc32c57994d00ba7ef3b1aa79825f
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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