Dimethylformamide → HCID 178429585, compound

HRID 2058124Notes

Reaction equation

HRID 2058124 reaction equation
[OH2:1].[ClH:2].[NH2:3][C@H:4]([C:12]([NH:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19]([CH3:26])=[CH:20][C:21](=[O:25])[O:22]2)=[CH:17][CH:16]=1)=[O:13])[CH2:5][CH2:6][CH2:7][NH:8][C:9](=[NH:11])[NH2:10].N[C@H](C(N[C:39]1[CH:48]=[C:47]2[C:42]([C:43](C)=[CH:44][C:45](=[O:49])O2)=[CH:41][CH:40]=1)=O)CCCNC(=N)N.Cl.C[N:53]([CH:55]=[O:56])C>O.C(O)(=O)C>[ClH:2].[C:55]([NH:53][C@H:44]([C:45]([NH:3][C@H:4]([C:12]([NH:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19]([CH3:26])=[CH:20][C:21](=[O:25])[O:22]2)=[CH:17][CH:16]=1)=[O:13])[CH2:5][CH2:6][CH2:7][NH:8][C:9](=[NH:10])[NH2:11])=[O:49])[CH2:43][C:42]1[CH:41]=[CH:40][CH:39]=[CH:48][CH:47]=1)([O:56][CH2:19][C:18]1[CH:23]=[CH:24][CH:15]=[CH:16][CH:17]=1)=[O:1]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 178429592HCID 178429592, compound

Product 1

HCID 178429585HCID 178429585, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

7-L-arginylamino-4-methylcoumarin hydrochloric acid salt hemihydrate (754 mg, 2 mM) was dissolved in a mixture of DMF (10 ml) and water (10 ml), and carbobenzoxy-L-phenylalanine N-hydroxysuccinimide ester (1.03 g, 2.6 mM) was added thereto. This mixture was stirred for 15 hours at room temperature and concentrated to yield a solid material. The material was purified by column chromatography (2×15 cm) using silica gel as adsorbent and a ternary mixture of chloroform, methylalcohol and acetic acid in 95:5:3 volume ratio. The main fraction was concentrated to yield solid material, dissolved in acetic acid (30 ml) and lyophilized to give 7-(Nα -carbobenzoxy-L-phenylalanyl-L-arginyl)amino-4-methylcoumarin hydrochloric acid salt [XV] (920 mg).

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. customto yield a solid material
  4. customThe material was purified by column chromatography (2×15 cm)
  5. additiona ternary mixture of chloroform, methylalcohol and acetic acid in 95:5:3 volume ratio
  6. concentrationThe main fraction was concentrated
  7. customto yield solid material

Sources & evidence

ORD record
ord-1e22131916004210adc33ee6d0bac3eb
Source dataset
uspto-grants-1980_07
Patent number
US04215047

Reaction notes

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