Diethylamine → benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate

HRID 2395104Notes

Reaction equation

HRID 2395104 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH3:79])([CH3:78])[C:8]3[C:13]([O:14][C:15]=2[C:16]=1[CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[C:12]([CH2:28][NH:29][C:30](=[O:75])[C@H:31]([CH3:74])[NH:32][C:33](=[O:73])[C@H:34]([CH2:61][C:62]1[CH:67]=[CH:66][C:65]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[CH:64][CH:63]=1)[NH:35][C:36](=[O:60])[C@H:37]([C@H:56]([CH2:58][CH3:59])[CH3:57])[NH:38]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[C:11]([O:76][CH3:77])=[CH:10][CH:9]=3.C(NCC)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH3:79])([CH3:78])[C:8]3[C:13]([O:14][C:15]=2[C:16]=1[CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])=[C:12]([CH2:28][NH:29][C:30](=[O:75])[C@H:31]([CH3:74])[NH:32][C:33](=[O:73])[C@H:34]([CH2:61][C:62]1[CH:67]=[CH:66][C:65]([O:68][C:69]([CH3:70])([CH3:71])[CH3:72])=[CH:64][CH:63]=1)[NH:35][C:36](=[O:60])[C@H:37]([C@H:56]([CH2:58][CH3:59])[CH3:57])[NH2:38])[C:11]([O:76][CH3:77])=[CH:10][CH:9]=3

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 18665271benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(N-(9H-fluoren-9-ylmethoxycarbonyl)-L-iso-leucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate

Product 1

HCID 67644872benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetateYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.74 g (0.73 mmol) of benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(N-(9H-fluoren-9-ylmethoxycarbonyl)-L-iso-leucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate in 7 ml of dimethylformamide was stirred at 0° for 1 hour in the presence of 0.7 ml of diethylamine. The reaction mixture was brought to dryness. The residue obtained was chromatographed over silica gel in chloroform/methanol, whereby 0.53 g of benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate was obtained; IR 3292, 2970, 1742, 1672, 1655, 1627, 1605, 1536, 1502, 1499 cm-1.

Workup

  1. customThe residue obtained
  2. customwas chromatographed over silica gel in chloroform/methanol

Sources & evidence

ORD record
ord-7edfed7d68634afdb7d09af92c76c72a
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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