Diisopropylethylamine → 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

HRID 2395103Notes

Reaction equation

HRID 2395103 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:24]([NH:26][C@H:27]([C:40]([NH:42][C@H:43]([C:45](O)=[O:46])[CH3:44])=[O:41])[CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:31][CH:30]=3)=[O:25])[C@H:20]([CH2:22][CH3:23])[CH3:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.[NH2:55][CH2:56][C:57]1[C:70]([O:71][CH3:72])=[CH:69][CH:68]=[C:67]2[C:58]=1[O:59][C:60]1[C:61]([CH2:77][C:78]([O:80][CH2:81][C:82]3[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=3)=[O:79])=[C:62]([O:75][CH3:76])[CH:63]=[CH:64][C:65]=1[C:66]2([CH3:74])[CH3:73].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH3:76][O:75][C:62]1[CH:63]=[CH:64][C:65]2[C:66]([CH3:74])([CH3:73])[C:67]3[C:58]([O:59][C:60]=2[C:61]=1[CH2:77][C:78]([O:80][CH2:81][C:82]1[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=1)=[O:79])=[C:57]([CH2:56][NH:55][C:45](=[O:46])[C@H:43]([CH3:44])[NH:42][C:40](=[O:41])[C@H:27]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[CH:33][CH:34]=1)[NH:26][C:24](=[O:25])[C@H:19]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH:18][C:16]([O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:17])[C:70]([O:71][CH3:72])=[CH:69][CH:68]=3

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18972493Benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetateHCID 54242266N-(9H-fluoren-9-ylmethoxycarbonyl)-L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanine

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.52 g (0.8 mmol) of N-(9H-fluoren-9-ylmethoxycarbonyl)-L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanine in 20 ml of dimethylformamide was cooled to 0° and treated with 0.45 g (0.8 mmol) of benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate and with 0.45 g (1.2 mmol) of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate. Thereafter, 0.31 g (2.4 mmol) of ethyldiisopropylamine was added, whereupon the reaction mixture obtained was warmed from 0° to room temperature within 3 hours and concentrated. The residue remaining was taken up in chloroform, whereupon the solution obtained was washed with water and dried over magnesium sulphate. After chromatography over silica gel (chloroform) 0.77 g of benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(N-(9H-fluoren-9-ylmethoxycarbonyl)-L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate of m.p. 218°-220° was obtained; IR 1728, 1662, 1606, 1503, 1492 cm-1.

Workup

  1. customobtained
  2. temperaturewas warmed from 0° to room temperature within 3 hours
  3. concentrationconcentrated
  4. customobtained
  5. washwas washed with water
  6. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-dd2286f60ba94f1e957623c1558e305d
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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