Trifluoroacetic acid → HCID 131725258, compound

HRID 1611423Notes

Reaction equation

HRID 1611423 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:10]([NH:12][C@H:13]([C:21]([NH:23][C@H:24]([C:32]([NH:34][C@@H:35]([C:46]([NH:48][C@H:49]([C:62]([NH:64][C@H:65]([C:69]([NH:71][C@H:72]([C:80]([NH:82][C@H:83]([C:87]([O:89][CH3:90])=[O:88])[C@@H:84]([CH3:86])[OH:85])=[O:81])[CH2:73][S:74][CH2:75][NH:76][C:77]([CH3:79])=[O:78])=[O:70])[C@@H:66]([CH3:68])[OH:67])=[O:63])[CH2:50][CH2:51][CH2:52][CH2:53][NH:54]C(OC(C)(C)C)=O)=[O:47])[CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:22])[CH2:14][S:15][CH2:16][NH:17][C:18]([CH3:20])=[O:19])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.SC(O)C.[C:102]([OH:108])([C:104]([F:107])([F:106])[F:105])=[O:103]>C(Cl)Cl>[NH2:1][C@@H:2]([C:10]([NH:12][C@H:13]([C:21]([NH:23][C@H:24]([C:32]([NH:34][C@@H:35]([C:46]([NH:48][C@H:49]([C:62]([NH:64][C@H:65]([C:69]([NH:71][C@H:72]([C:80]([NH:82][C@H:83]([C:87]([O:89][CH3:90])=[O:88])[C@@H:84]([CH3:86])[OH:85])=[O:81])[CH2:73][S:74][CH2:75][NH:76][C:77]([CH3:79])=[O:78])=[O:70])[C@@H:66]([CH3:68])[OH:67])=[O:63])[CH2:50][CH2:51][CH2:52][CH2:53][NH2:54])=[O:47])[CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)=[O:33])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:22])[CH2:14][S:15][CH2:16][NH:17][C:18]([CH3:20])=[O:19])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:105][C:104]([C:102]([OH:108])=[O:103])([F:107])[F:106]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4713212Mercapto-ethanolHCID 131725260HCID 131725260, compound

Product 1

HCID 131725258HCID 131725258, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The octapeptide ester XVIII (11 g, 7.9 mm anisole, 2 ml) and mercaptoethanol (2 ml) are suspended in DCM (20 ml) under N2. The suspension is cooled to 0° C. and TFA (80 ml) is added. Stirring is continued for one and half hour at same temperature. The TFA and DCM are evaporated under vacuum at 30° C., ether (200 ml) is added to the residue under stirring. The precipitates are filtered, washed with diethyl ether (300 ml) and dried in vacuum to give compound XIX: Yield 10.0 g (91%). ESMS=1191 (M+H). H-(D)-Phe-Cys(Acm)-Phe-(D)-Trp-Lys-Thr-Cys(Acm)-Throninol·2TFA  (XVI)

Workup

  1. customis continued for one and half hour at same temperature
  2. customThe TFA and DCM are evaporated under vacuum at 30° C.
  3. additionether (200 ml) is added to the residue
  4. stirringunder stirring
  5. filtrationThe precipitates are filtered
  6. washwashed with diethyl ether (300 ml)
  7. customdried in vacuum

Sources & evidence

ORD record
ord-592faaeff08b4f64bd3ef260282c3033
Source dataset
uspto-grants-2006_01
Patent number
US06987167B2

Reaction notes

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