N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → HCID 67346526, compound

HRID 1669443Notes

Reaction equation

HRID 1669443 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:11][N:10]2[C:12]3[CH:13]=[C:14]([C:25]([O:27][CH3:28])=[O:26])[CH:15]=[CH:16][C:17]=3[C:18]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:9]2[C:8]2[CH:29]=[CH:30][CH:31]=[CH:32][C:7]=2[O:6][CH2:5]1.[C:33]([O:37][C:38]([NH:40][CH2:41][CH2:42][C:43](O)=[O:44])=[O:39])([CH3:36])([CH3:35])[CH3:34].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[C:33]([O:37][C:38]([NH:40][CH2:41][CH2:42][C:43]([NH:1][CH2:2][CH2:3][CH:4]1[CH2:11][N:10]2[C:12]3[CH:13]=[C:14]([C:25]([O:27][CH3:28])=[O:26])[CH:15]=[CH:16][C:17]=3[C:18]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)=[C:9]2[C:8]2[CH:29]=[CH:30][CH:31]=[CH:32][C:7]=2[O:6][CH2:5]1)=[O:44])=[O:39])([CH3:36])([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66675025HCID 66675025, compound

Product 1

HCID 67346526HCID 67346526, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 7(R,S)-(2-aminoethyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.14 M) in DCM was treated with N-(tert-butoxycarbonyl)-β-alanine (2 eq) followed by HATU (1.3 eq) and DIPEA (2.5 eq) and the resulting mixture was stirred overnight at RT. The reaction was diluted with EtOAc and the combined organic layers were washed with sat. aq. NaHCO3, HCl (1N) and brine, before being dried (Na2SO4), filtered and concentrated in vacuo. The product was used directly in the next step without further purification. (ES+) m/z 604 (M+H)+.

Workup

  1. washthe combined organic layers were washed with sat. aq. NaHCO3, HCl (1N) and brine
  2. dry with materialbefore being dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was used directly in the next step without further purification

Sources & evidence

ORD record
ord-9b63b56d0e6c49daaf6bfd307c9bcc6d
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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