Citric Acid → HCID 13503172, compound

HRID 371356Notes

Reaction equation

HRID 371356 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH:31][C@H:32]([C:40]([NH2:42])=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:30])[CH2:25][C:26](=[O:28])[OH:27])=[O:22])[CH2:17][CH2:18][S:19][CH3:20])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH:50]([C:72]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])=[O:73])[C@H:51]([C:62]([O:64]N1C(=O)CCC1=O)=O)[CH2:52][C:53]1[C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[NH:55][CH:54]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[NH:50]([C:72]([O:74][C:75]([CH3:76])([CH3:77])[CH3:78])=[O:73])[C@@H:51]([C:62]([NH:1][C@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH:31][C@H:32]([C:40]([NH2:42])=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:30])[CH2:25][C:26](=[O:27])[OH:28])=[O:22])[CH2:17][CH2:18][S:19][CH3:20])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)=[O:64])[CH2:52][C:53]1[C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[NH:55][CH:54]=1

Participants

4

Reactant 3

HCID 311Citric AcidHCID 98767tert-Butyl (S)-(2-((2,5-dioxo-1-pyrrolidinyl)oxy)-1-(1H-indol-3-ylmethyl)-2-oxoethyl)carbamateHCID 13178389HCID 13178389, compound2×

Product 1

HCID 13503172HCID 13503172, compoundYield 61.1%

Procedure

In the same manner as in (1) of Example 1, 10.45 g (0.015 mole) of Boc-Trp-Met-Asp-Phe-NH2 [cf. (1) of Example 3] was condensed with 9.00 g (0.022 mole) of Boc-Trp-OSu. The resulting reaction liquid was concentrated, and a precipitate was formed by adding 1N citric acid and washed with water. Recrystallization thereof from methanol-water gave 8.09 g of Boc-D-Trp-Trp-Met-Asp-Phe-NH2 ; yield 61.1%, m.p. 225°-227° C.

Workup

  1. customThe resulting reaction liquid
  2. concentrationwas concentrated
  3. customa precipitate was formed
  4. washwashed with water
  5. customRecrystallization

Sources & evidence

ORD record
ord-8f7df928581c4c4382ec33b6a8475b6b
Source dataset
uspto-grants-1985_07
Patent number
US04530836

Reaction notes

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