HCID 56990923, compound → HCID 70618367, compound

HRID 838877Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:69])[C@H:4]([CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[NH:5][C:6](=[O:61])[C@H:7]([CH2:53][C:54]1[CH:59]=[CH:58][C:57]([OH:60])=[CH:56][CH:55]=1)[NH:8][C:9](=[O:52])[C@H:10]([CH2:31][S:32][C:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH:11]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(O)(=O)C.O>[CH3:1][O:2][C:3](=[O:69])[C@H:4]([CH2:62][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)[NH:5][C:6](=[O:61])[C@H:7]([CH2:53][C:54]1[CH:59]=[CH:58][C:57]([OH:60])=[CH:56][CH:55]=1)[NH:8][C:9](=[O:52])[C@H:10]([CH2:31][S:32][C:33]([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[NH2:11]

Participants

Conditions

Temperature: 45 °C

Procedure

Water (445 ml) is added dropwise to a solution of N,S-ditrityl-cysteinyl-tyrosyl-phenylalanine methyl ester (21.9 g, 23.5 mmoles, described in Example 1) in glacial acetic acid (1780 ml) at room temperature. The solution is stirred at 45° C for 1.5 hour and diluted with water (2200 ml). The precipitate is removed by filtration and the filtrate is evaporated. The last traces of acetic acid are removed by repeated evaporation with benzene to give (S-trityl)cysteinyl-tyrosyl-phenylalanine methyl ester.

Workup

customThe precipitate is removed by filtration
customthe filtrate is evaporated
customThe last traces of acetic acid are removed
customevaporation with benzene

Sources & evidence

ORD record: ord-c6738fb711ff4325b3c1baaba5ae367f
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04093610

Reaction notes

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