Dimethylformamide → HCID 70074385, compound

HRID 1378245Notes

Reaction equation

HRID 1378245 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[C:13](NCC(O)=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[NH2:25]/[C:26](=[N:44]\[OH:45])/[C:27]1[N:28]=[CH:29][N:30]2[C:36]3[CH:37]=[CH:38][S:39][C:35]=3[C:34](=[O:40])[N:33]3[CH2:41][CH2:42][CH2:43][C@H:32]3[C:31]=12.[CH3:46]N(C)C=O>>[C:13]([C:46]1[O:45][N:44]([CH2:1][NH2:3])[CH:26]([C:27]2[N:28]=[CH:29][N:30]3[C:36]4[CH:37]=[CH:38][S:39][C:35]=4[C:34](=[O:40])[N:33]4[CH2:41][CH2:42][CH2:43][C@H:32]4[C:31]=23)[N:25]=1)([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 88136046HCID 88136046, compound

Product 1

HCID 70074385HCID 70074385, compoundYield 44%

Procedure

1.40 g (8.04 mmol) of 1,1'-carbonyldiimidazole were added to a solution of 1.42 g (8.07 mmol) of BOC-glycine in 13 ml of dimethylformamide and the mixture was stirred at 50° for 30 minutes. Subsequently, 2.30 g (7.58 mmol) of (E)- and/or (Z)- (S)-1-(aminohydroxyimino-methyl)-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo-[1,2-a]thieno[3,2-e][1,4]diazepin-8-one were added thereto and the mixture was stirred at 90° for 15 hours. The brown solution obtained was evaporated in a high vacuum and the brown residue obtained was chromatographed (silica gel, methylene chloride/methanol 10:1). There were obtained 1.50 g (44%) of (S)-1-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-8-one as a colourless foam, Rf=0.62 (silica gel, methylene chloride/methanol 10:1).

Workup

  1. stirringthe mixture was stirred at 90° for 15 hours
  2. customThe brown solution obtained
  3. customwas evaporated in a high vacuum
  4. customthe brown residue obtained
  5. customwas chromatographed (silica gel, methylene chloride/methanol 10:1)

Sources & evidence

ORD record
ord-d274d737c79f4cf78058ba7ed43eb537
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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