Sodium Chloride → HCID 131718368, compound

HRID 1077690Notes

Reaction equation

HRID 1077690 reaction equation
[CH:1]1[CH:6]=[C:5]([NH:7][C:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[C:23]4[N:24]=[CH:25][N:26]([C@@H:27]5[O:31][C@H:30]([CH2:32][OH:33])[C@@H:29]([OH:34])[C@H:28]5[OH:35])[C:22]=4[N:21]=[CH:20][N:19]=3)=[CH:13][CH:12]=2)=[O:9])[CH:4]=[C:3]([CH2:36][C:37]([NH:39][CH2:40][CH2:41][NH2:42])=[O:38])[CH:2]=1.C(N(CC)CC)C.C(Cl)(Cl)=S.[Cl-:54].[Na+].CN(C)C=[O:59]>O>[CH:1]1[CH:6]=[C:5]([NH:7][C:8]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:18]3[C:23]4[N:24]=[CH:25][N:26]([C@@H:27]5[O:31][C@H:30]([CH2:32][OH:33])[C@@H:29]([OH:34])[C@H:28]5[OH:35])[C:22]=4[N:21]=[CH:20][N:19]=3)=[CH:15][CH:16]=2)=[O:9])[CH:4]=[C:3]([CH2:36][C:37]([NH:39][CH2:40][CH2:41][NH2:42])=[O:38])[CH:2]=1.[CH2:36]1[C:37](=[O:38])[N:39]([Cl:54])[C:40](=[O:59])[CH2:41]1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 16218845N-[3-[2-(2-aminoethylamino)-2-oxoethyl]phenyl]-2-[4-[[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]phenyl]acetamide

Product 1

HCID 131718368HCID 131718368, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

ADAC, 25 mg, 43 micromol, and 6 microliters triethylamine were dissolved in 1 ml dimethylformamide with warming. After cooling in an ice bath, 3.9 microl, 51 micromol of distilled thiophosgene was added with stirring. Water and saturated sodium chloride were added to obtain a white precipitate-, which was dried in vacuo over sodium hydroxide. The yield was 13 mg, or 48%, of product. IR peaks appeared at 3460, 2120, 1640, 1600, 1515, 1480, 1420, 1100, 1060, and 1030 cm-1. Thin layer chromatography and the Cf plasma desorption spectrum was consistent with the assigned structure and showed no evidence of residual ADAC.

Workup

  1. temperaturewith warming
  2. temperatureAfter cooling in an ice bath
  3. customto obtain a white precipitate-, which
  4. dry with materialwas dried in vacuo over sodium hydroxide

Sources & evidence

ORD record
ord-a731c5e6affa49f49b0b5a02a8f11d76
Source dataset
uspto-grants-1996_08
Patent number
US05545627

Reaction notes

Loading…