Trifluoroacetic acid → HCID 86750654, compound

HRID 53060Notes

Reaction equation

HRID 53060 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C@H:9]1[CH2:44][C@@:43]2([CH3:45])[C@@H:20]([CH2:21][CH2:22][C@:23]2([O:46][C:47](=[O:50])[CH2:48][CH3:49])[C:24](=[O:42])[CH:25]([O:27][C:28](=[O:41])[C@H:29]([CH:38]([CH3:40])[CH3:39])[NH:30]C(OC(C)(C)C)=O)[OH:26])[C@H:19]2[C@H:10]1[C@:11]1([CH3:53])[C:16]([C@@H:17]([CH3:51])[CH2:18]2)=[CH:15][C:14](=[O:52])[CH:13]=[CH:12]1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C@H:9]1[CH2:44][C@@:43]2([CH3:45])[C@@H:20]([CH2:21][CH2:22][C@:23]2([O:46][C:47](=[O:50])[CH2:48][CH3:49])[C:24](=[O:42])[CH:25]([O:27][C:28](=[O:41])[C@H:29]([CH:38]([CH3:39])[CH3:40])[NH2:30])[OH:26])[C@H:19]2[C@H:10]1[C@:11]1([CH3:53])[C:16]([C@@H:17]([CH3:51])[CH2:18]2)=[CH:15][C:14](=[O:52])[CH:13]=[CH:12]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86750656N-(1,1-dimethylethoxycarbonyl)valine [11beta,21-dihydroxy-3,20-dioxo-6alpha-methyl-17-propionyloxy-pregna-1,4-dien-21-yl] ester

Product 1

HCID 86750654HCID 86750654, compoundYield 80%

Procedure

Under initial cooling, 5 ml of trifluoroacetic acid is poured over 896 mg (1.42 mmol) of N-(1,1-dimethylethoxycarbonyl)valine [11β,21-dihydroxy-3,20-dioxo-6α-methyl-17-propionyloxy-pregna-1,4-dien-21-yl] ester, and it is stirred for 1-2 hours at room temperature. Then, the trifluoroacetic acid is evaporated in a vacuum. The residue is taken up in a little dichloromethane, 5 ml of toluene is added and then evaporated to dryness in a vacuum. The residue is crystallized. 728 mg (80%) of valine [11β,21-dihydroxy-3,20-dioxo-6α-methyl-17-propionyloxy -pregna-1,4-dien-21-yl] ester trifluoroacetate is obtained. Melting point 148° C.

Workup

  1. temperatureUnder initial cooling
  2. customThen, the trifluoroacetic acid is evaporated in a vacuum
  3. additionis added
  4. customevaporated to dryness in a vacuum
  5. customThe residue is crystallized

Sources & evidence

ORD record
ord-468ef4c572d441718aaea53408d681ed
Source dataset
uspto-grants-1997_04
Patent number
US05616573

Reaction notes

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