N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → HCID 67040268, compound

HRID 605120Notes

Reaction equation

HRID 605120 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=3)=[O:14])=[CH:11][C:10]=2[NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:4][CH:3]=1.C(OC([NH:46][CH2:47][CH2:48][C:49](O)=[O:50])=O)(C)(C)C.N(C(OC(C)(C)C)=O)[C@H](C(O)=O)CC>>[NH2:46][CH2:47][CH2:48][C:49]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([Br:22])=[CH:20][CH:21]=3)=[O:14])=[CH:11][C:10]=2[NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:4][CH:3]=1)=[O:50]

Participants

4

Reactant 3

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanine2×HCID 2755934(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acidHCID 67040834HCID 67040834, compound

Product 1

HCID 67040268HCID 67040268, compoundYield 23%

Procedure

The product of Example 13E was reacted with 3-tert-Butoxycarbonylamino-propionic acid using the procedure of Example 70 substituting 3-tert-Butoxycarbonylamino-propionic acid for Boc-Abu-OH to provide the crude title compound which was purified by HPLC with TFA then neutralized with an aqueous sodium carbonate solution to provide the title compound (15 mg, 23%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.33 (d, J=6.62 Hz, 6 H) 2.41 (t, J=6.25 Hz, 2 H) 2.83 (t, J=6.25 Hz, 2 H) 3.20 (m, 1 H) 6.97 (d, J=8.46 Hz, 1 H) 7.39 (d, J=8.46 Hz, 2 H) 7.54 (m, 3 H) 7.70 (m, 5 H) 7.95 (s, 1 H) 8.47 (s, 1 H) 8.79 (d, J=8.09 Hz, 1 H) 10.32 (s, 1 H); MS (ESI+) m/z 656/658 (M+H)+.

Workup

  1. customto provide the crude title compound which
  2. customwas purified by HPLC with TFA

Sources & evidence

ORD record
ord-dbe08ede78ee4d93b41ee20732852010
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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