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HCID 56990923, compound → HCID 70618367, compound

HRID 838877
Notes
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Reaction equation

HRID 838877 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 56990923HCID 56990923, compound

Product 1

HCID 70618367HCID 70618367, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

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

  1. customThe precipitate is removed by filtration
  2. customthe filtrate is evaporated
  3. customThe last traces of acetic acid are removed
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes