Dimethylformamide → HCID 67111918, compound

HRID 1914806Notes

Reaction equation

HRID 1914806 reaction equation
CCN(C(C)C)C(C)C.CN(C(ON1N=[N:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24]C1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[C:33]1([C:41]2[CH:46]=[CH:45]C=[CH:43][CH:42]=2)[CH:38]=[CH:37][C:36](NC)=[CH:35][CH:34]=1.[CH3:47][N:48]([CH:50]=[O:51])[CH3:49]>>[C:41]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:42]=[CH:43][C:47]([N:48]([CH3:49])[C:50]([C@@H:23]2[CH2:22][CH2:21][C@H:20]([NH2:25])[CH2:24]2)=[O:51])=[CH:45][CH:46]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 23207854861556-02-7

Product 1

HCID 67111918HCID 67111918, compound

Procedure

351.4 mg (1.00 mmol) (1S,3R)—(N)-Fmoc-1-aminocyclopentane-3-carboxylic acid is stirred in DMF at RT. 500.0 mg (4.00 mmol) DIPEA and 417.3 mg (1.3 mmol) TBTU are added. 219.0 mg (1.0 mmol) Biphenyl-4-yl-methyl-amine hydrochloride (II.1.c) is added and the mixture is stirred at RT over night. The solvent is evaporated. The product is purified by RP-HPLC (water+5-95% acetonitrile (with addition of 0.1% TFA)) and lyophilized. The residue is taken up in DCM and diethylamine is added. After 2 hours of stirring at RT the mixture is filtered and evaporated.

Workup

  1. customThe solvent is evaporated
  2. customThe product is purified by RP-HPLC (water+5-95% acetonitrile (with addition of 0.1% TFA))
  3. additiondiethylamine is added
  4. stirringAfter 2 hours of stirring at RT the mixture
  5. filtrationis filtered
  6. customevaporated

Sources & evidence

ORD record
ord-dce50e52891b4d35abe7c54f1254a844
Source dataset
uspto-grants-2013_12
Patent number
US08614238B2

Reaction notes

Loading…