Trimethyl orthoformate → HCID 67344869, compound

HRID 1669418Notes

Reaction equation

HRID 1669418 reaction equation
[NH2:1][C@@H:2]1[CH2:9][N:8]2[C:10]3[CH:11]=[C:12]([C:23]([O:25][CH3:26])=[O:24])[CH:13]=[CH:14][C:15]=3[C:16]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:7]2[C:6]2[CH:27]=[CH:28][C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)=[CH:30][C:5]=2[O:4][CH2:3]1.C(OC)(OC)OC.[CH3:46][N:47]([CH2:55][CH:56]=O)[C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51].[BH3-]C#N.[Na+]>>[C:50]([O:49][C:48]([N:47]([CH3:46])[CH2:55][CH2:56][NH:1][C@@H:2]1[CH2:9][N:8]2[C:10]3[CH:11]=[C:12]([C:23]([O:25][CH3:26])=[O:24])[CH:13]=[CH:14][C:15]=3[C:16]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:7]2[C:6]2[CH:27]=[CH:28][C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)=[CH:30][C:5]=2[O:4][CH2:3]1)=[O:54])([CH3:53])([CH3:52])[CH3:51]

Participants

5

Reactant 4

HCID 9005Trimethyl orthoformate2×HCID 5003444Sodium cyanoborohydrideHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 67343088HCID 67343088, compound

Product 1

HCID 67344869HCID 67344869, compound

Procedure

Methyl (7R)-7-amino-14-cyclohexyl-3-(pyridin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate was dissolved in HC(OMe)3 (50 eq) and a solution of tert-butyl methyl(2-oxoethyl)carbamate (1.6 eq, prepared according to Tetrahedron 2002, 58, 1719-1737) in HC(OMe)3 (50 eq) was added. The mixture was stirred overnight at RT to allow formation of the imine. All volatiles were evaporated and the residual material was dissolved in MeOH/HOAc (0.05 M). NaCNBH3 (1 eq) was added and the mixture was stirred at RT for 1 h. Some formation of the N-formyl product was observed alongside formation of the desired product. The solution was used directly in the next step. (ES+) m/z 669 (M+H)+.

Workup

  1. customAll volatiles were evaporated
  2. dissolutionthe residual material was dissolved in MeOH/HOAc (0.05 M)
  3. stirringthe mixture was stirred at RT for 1 h

Sources & evidence

ORD record
ord-77455aacb64f46938decc0512f161b5c
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

Loading…