Hydrochloric Acid → HCID 131714158, compound

HRID 2164484Notes

Reaction equation

HRID 2164484 reaction equation
[NH:1]([C:103]([CH3:105])=[O:104])[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:31]([NH:33][C@H:34]([C:38]([NH:40][C@H:41]([C:50]([NH:52][C@H:53]([C:61]([NH:63][C@H:64]([C:71]([NH:73][C@H:74]([C:81]([NH:83][C@H:84]([C:94]([O:96]C1C=CC=CC=1)=[O:95])[CH2:85][CH2:86][C:87](=[O:93])[O:88][C:89]([CH3:92])([CH3:91])[CH3:90])=[O:82])[CH2:75][O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:72])[CH2:65][O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:62])[C@@H:54]([CH3:60])[O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:51])[CH2:42][C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:39])[CH:35]([CH3:37])[CH3:36])=[O:32])[CH3:30])=[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:103]([CH3:105])=[O:104])[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:31]([NH:33][C@H:34]([C:38]([NH:40][C@H:41]([C:50]([NH:52][C@H:53]([C:61]([NH:63][C@H:64]([C:71]([NH:73][C@H:74]([C:81]([NH:83][C@H:84]([C:94]([OH:96])=[O:95])[CH2:85][CH2:86][C:87](=[O:93])[O:88][C:89]([CH3:92])([CH3:91])[CH3:90])=[O:82])[CH2:75][O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:72])[CH2:65][O:66][C:67]([CH3:68])([CH3:69])[CH3:70])=[O:62])[C@@H:54]([CH3:60])[O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:51])[CH2:42][C:43](=[O:49])[O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:39])[CH:35]([CH3:37])[CH3:36])=[O:32])[CH3:30])=[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]([CH3:7])([CH3:8])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2×HCID 131714157HCID 131714157, compound

Product 1

HCID 131714158HCID 131714158, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of Ac-Ser(tBu)-Asp(OtBu)-Ala-Ala-Val-Asp(OtBu)-Thr(tBu)-Ser(tBu)-Ser(tBu)-Glu(OtBu)-OC6H5 (22.73 g, 15.2 mmol) in TFE: H2O (270 mL: 20 mL) was treated with 3% H2O2 (15.5 ml, 15.2 mmol, 1 eq.) with stirring (magnetic). The reaction mixture was adjusted to pH 10.5 by addition of 1N NaOH and maintained at pH 10.5 over a period of 3 h by addition of 1N NaOH (triggered by an autotitrator). The reaction mixture was adjusted to pH 3 (1N HCl), filtered and the solid washed with H2O (200 mL) and dried in vacuo. Yield: 21.85 g (98.8%); mp >245° dec; [α]D25 -16.31° (c 0.4, TFE); Rf 0.67 (CHCl3 :MeOH:AcOH; 85-10-5). Amino Acid Anal. (6M HCl, 110°, 24 h): Asp (1.99); Thr (0.96); Ser (2.83); Glu (1.02); Ala (1.99); Val (1.01). Anal. calc. for C67H118N10O22.2H2O (1451.79): C, 55.43; H, 8.19; N, 9.65. Found: C, 55.24; H, 8.24; N, 9.56.

Workup

  1. filtrationfiltered
  2. washthe solid washed with H2O (200 mL)
  3. customdried in vacuo
  4. custom(6M HCl, 110°, 24 h)

Sources & evidence

ORD record
ord-44910595e4ed43138b426d18a1128312
Source dataset
uspto-grants-1985_03
Patent number
US04504415

Reaction notes

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