Diisopropylethylamine → 5-[N-(tert-butyloxycarbonyl)aminomethyl]-3,6-dimethoxy-9,9-dimethoxyxanthene-4-acetic acid (O-benzyl-L-glutamyl)amide

HRID 2395110Notes

Reaction equation

HRID 2395110 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]2[C:11]=1[O:12][C:13]1[C:14]([CH2:30][C:31](O)=[O:32])=[C:15]([O:28][CH3:29])[CH:16]=[CH:17][C:18]=1[C:19]2(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:35]([O:42][C:43](=[O:51])[C@H:44]([CH2:46][CH2:47][C:48](=[O:50])[NH2:49])N)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.F[P-](F)(F)(F)(F)F.N1([O:68][C:69](N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C([N:79](C(C)C)CC)(C)C.[C:85](=[O:88])(O)[O-].[Na+]>CN(C)C=O>[CH2:35]([O:42][C:43](=[O:51])[CH2:44][CH2:46][C@@H:47]([C:48]([NH:49][C:31](=[O:32])[CH2:30][C:14]1[C:13]2[O:12][C:11]3[C:20](=[CH:21][CH:22]=[C:23]([O:24][CH3:25])[C:10]=3[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:19]([O:68][CH3:69])([O:88][CH3:85])[C:18]=2[CH:17]=[CH:16][C:15]=1[O:28][CH3:29])=[O:50])[NH2:79])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 676449095-[(1-Tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acidHCID 70076807(S)-Benzyl 2,5-diamino-5-oxopentanoate hydrochloride

Product 1

HCID 1317208425-[N-(tert-butyloxycarbonyl)aminomethyl]-3,6-dimethoxy-9,9-dimethoxyxanthene-4-acetic acid (O-benzyl-L-glutamyl)amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.46 g of 5-[(1-tert-butoxyformamido)-methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid and 0.3 g of O-benzyl-L-glutamine hydrochloride in 10 ml of dimethylformamide was cooled to 0° and treated firstly with 0.45 g of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate and then with 0.37 ml of diisopropylethylamine. The solution obtained was warmed to room temperature, stirred for 2 hours and then poured into dilute sodium bicarbonate solution. The separated precipitate was filtered off, washed with water and dried in a vacuum, whereby 0.59 g of 5-[N-(tert-butyloxycarbonyl)aminomethyl]-3,6-dimethoxy-9,9-dimethoxyxanthene-4-acetic acid (O-benzyl-L-glutamyl)amide was obtained; MS: 676 (M+H)+.

Workup

  1. customThe solution obtained
  2. filtrationThe separated precipitate was filtered off
  3. washwashed with water
  4. customdried in a vacuum

Sources & evidence

ORD record
ord-b0c54d6fcd7040fc8b1e03db773d0958
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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