Dimethylformamide → HCID 131719590, compound

HRID 864098Notes

Reaction equation

HRID 864098 reaction equation
[C:1]([NH:8][C@H:9](C(O)=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH2:23].ON1[C:29]2C=CC=C[C:28]=2N=N1.Cl.CN(C)[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]N=C=N.[C:46](O)([C:48](F)(F)F)=[O:47].C[N:54]1[CH2:59]CO[CH2:56][CH2:55]1.[Cl-].[Na+].O.O.C[N:65]([CH3:68])[CH:66]=[O:67]>>[CH3:7][C:4]([CH3:5])([O:3][C:1]([NH:8][C@H:9]([C:66]([NH:65][C@@H:68]([C:59]([NH:54][CH:55]([CH3:56])[CH2:37][C:38]1[CH:29]=[CH:28][CH:41]=[CH:40][CH:39]=1)=[O:23])[C@H:46]([CH3:48])[OH:47])=[O:67])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)=[O:2])[CH3:6]

Participants

8

Reactant 7

HCID 6228Dimethylformamide2×HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 27960291-Hydroxybenzotriazole hydrateHCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanineHCID 23713072Sodium chloride dihydrateHCID 574828161-(3-Dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride

Product 1

HCID 131719590HCID 131719590, compoundYield 98%

Procedure

To a solution of Part A compound (0.418 g, 1.29 mmol, 1.00 eq.) in dichloromethane (2.2 mL) under argon at 0° C. was added trifluoroacetic acid (1.5 mL, 19.5 mmol, 15.1 eq.). After 4.0 hr, trifluoroacetic acid (5 mL, 64.8 mmol, 5.44 eq.) was added. After 5 hr, the reaction mixture was concentrated in vacuo to give the crude TFA salt of Part A compound. To a solution of Boc-4-nitro-L-phenylalanine (0.441 g, 1.42 mmol, 1.10 eq.) and 1-hydroxybenzo-triazole hydrate (0.193 g, 1.43 mmol, 1.10 eq.) in dimethylformamide (5.0 mL) at 0° C. was added 1-(3-dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride (0.273 g, 1.43 mmol, 1.10 eq.). After 0.5 hr, a solution of crude TFA salt of Part A compound (1.29 mmol, 1.00 eq.) in dimethylformamide (3.0 mL) was added, which was then followed by 4-methylmorpholine (0.5 mL, 4.55 mmol, 3.52 eq.). After 21 hr, the reaction mixture was poured into a brine/water solution (1:1) and extracted with ethyl acetate twice. The organic layers were combined and washed with aqueous 0.25M potassium hydrogen sulfate, water, aqueous saturated sodium bicarbonate and water, successively. The organic layer was concentrated in vacuo to give title compound (0.651 g, 98.0%):

Workup

  1. waitAfter 21 hr
  2. extractionextracted with ethyl acetate twice
  3. washwashed with aqueous 0.25M potassium hydrogen sulfate, water, aqueous saturated sodium bicarbonate and water
  4. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-6517ef4b1f8d4574806198650a083288
Source dataset
uspto-grants-1996_10
Patent number
US05561146

Reaction notes

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