Hydrochloric Acid → HCID 131714162, compound

HRID 2164487Notes

Reaction equation

HRID 2164487 reaction equation
[NH:1]([C:105]([O:107][C:108]([CH3:111])([CH3:110])[CH3:109])=[O:106])[C@H:2]([C:9]([NH:11][C@H:12]([C:21]([NH:23][C@H:24]([C:26]([NH:28][C@H:29]([C:33]([NH:35][C@H:36]([C:40]([NH:42][C@H:43]([C:52]([NH:54][C@H:55]([C:63]([NH:65][C@H:66]([C:73]([NH:75][C@H:76]([C:83]([NH:85][C@H:86]([C:96]([O:98]C1C=CC=CC=1)=[O:97])[CH2:87][CH2:88][C:89](=[O:95])[O:90][C:91]([CH3:94])([CH3:93])[CH3:92])=[O:84])[CH2:77][O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:74])[CH2:67][O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:64])[C@@H:56]([CH3:62])[O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:53])[CH2:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:41])[CH:37]([CH3:39])[CH3:38])=[O:34])[CH:30]([CH3:32])[CH3:31])=[O:27])[CH3:25])=[O:22])[CH2:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:10])[CH2:3][O:4][C:5]([CH3:8])([CH3:7])[CH3:6].OO.[OH-].[Na+].Cl>O>[NH:1]([C:105]([O:107][C:108]([CH3:109])([CH3:110])[CH3:111])=[O:106])[C@H:2]([C:9]([NH:11][C@H:12]([C:21]([NH:23][C@H:24]([C:26]([NH:28][C@H:29]([C:33]([NH:35][C@H:36]([C:40]([NH:42][C@H:43]([C:52]([NH:54][C@H:55]([C:63]([NH:65][C@H:66]([C:73]([NH:75][C@H:76]([C:83]([NH:85][C@H:86]([C:96]([OH:98])=[O:97])[CH2:87][CH2:88][C:89](=[O:95])[O:90][C:91]([CH3:94])([CH3:93])[CH3:92])=[O:84])[CH2:77][O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:74])[CH2:67][O:68][C:69]([CH3:70])([CH3:71])[CH3:72])=[O:64])[C@@H:56]([CH3:62])[O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:53])[CH2:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:41])[CH:37]([CH3:38])[CH3:39])=[O:34])[CH:30]([CH3:32])[CH3:31])=[O:27])[CH3:25])=[O:22])[CH2:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:10])[CH2:3][O:4][C:5]([CH3:7])([CH3:8])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 131714163HCID 131714163, compound

Product 1

HCID 131714162HCID 131714162, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of Boc-Ser(tBu)-Asp(OtBu)-Ala-Val-Val-Asp(OtBu)-Thr(tBu)-Ser(tBu)-Ser(tBu)-Glu(OtBu)-OC6H5 (452 mg, 0.29 mmol) in TFE:H2O (5.2-0.4 mL) was treated with 3% H2O2 (0.31 mL, 0.30 mmol, 1.0 eq) with stirring (magnetic). The reaction mixture was adjusted to pH 10.5 by addition of 1N NaOH (triggered by an autotitrator) and maintained at that pH for 3 h. The reaction mixture was adjusted to pH ~1 with 1M HCl, refrigerated, filtered and washed with H2O and CH3OH and dried in vacuo. Yield: 423 mg (98.4%); mp ~245° dec; [α]D25 -13.28° (c 1, TFE); Rf 0.41 (CHCl3 :MeOH:AcOH; 80-2-0.4). Anal. calc. for C70H127N10O23.H2O (1494.87): C, 56.24; H, 8.69; N, 9.37. Found: C, 56.33; H, 8.32; N, 9.24.

Workup

  1. temperaturemaintained at that pH for 3 h
  2. filtrationfiltered
  3. washwashed with H2O and CH3OH
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3f9a2272c62a4c4585b53534d83f4a06
Source dataset
uspto-grants-1985_03
Patent number
US04504415

Reaction notes

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