Phenol → [(S)-1-(2-{(4-Phenoxyphenyl)-[(E)-(3-phenylacryloyl)]amino}acetyl)pyrrolidin-3-yl]carbamic acid, tert-butyl ester

HRID 2243986Notes

Reaction equation

HRID 2243986 reaction equation
C(N(CC)CC)C.B([C:11]1[CH:16]=[CH:15][C:14]([N:17]([C:34](=[O:43])/[CH:35]=[CH:36]/[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:18][C:19]([N:21]2[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22]2)=[O:20])=[CH:13][CH:12]=1)(O)O.[C:44]1([OH:50])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>ClCCl>[O:50]([C:11]1[CH:16]=[CH:15][C:14]([N:17]([C:34](=[O:43])/[CH:35]=[CH:36]/[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:18][C:19]([N:21]2[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22]2)=[O:20])=[CH:13][CH:12]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 8471TriethylamineHCID 59211964[(S)-1-(2-{(4-borono-phenyl)-[(E)-(3-phenylacryloyl)]amino}acetyl)pyrrolidin-3-yl]carbamic acid, tert-butyl ester

Product 1

HCID 59211991[(S)-1-(2-{(4-Phenoxyphenyl)-[(E)-(3-phenylacryloyl)]amino}acetyl)pyrrolidin-3-yl]carbamic acid, tert-butyl esterYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.13 mL, 0.91 mmol) was added to [(S)-1-(2-{(4-borono-phenyl)-[(E)-(3-phenylacryloyl)]amino}acetyl)pyrrolidin-3-yl]carbamic acid, tert-butyl ester 5 (90 mg, 0.18 mmol), copper[II]acetate, 4 Å sieve (powdered) and phenol (26 mg, 0.27 mmol) in dichloromethane (4 mL). The reaction mixture was stirred at room temperature for 16 h and then diluted with dichloromethane and washed with 10% hydrochloric acid, 1M NaOH (×2) and brine, dried (Na2SO4) and evaporated to dryness. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/petrol (2:1), to give the title compound as a white powder (60 mg) which was used directly in the next stage.

Workup

  1. washwashed with 10% hydrochloric acid, 1M NaOH (×2) and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated to dryness
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with ethyl acetate/petrol (2:1)

Sources & evidence

ORD record
ord-4d73ee08e68a4b0b9bbf3e076c3a77ef
Source dataset
uspto-grants-2010_03
Patent number
US07678785B2

Reaction notes

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