Hydrochloric Acid → HCID 86688739, compound

HRID 1752639Notes

Reaction equation

HRID 1752639 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]2[C:39]([C:40]3[CH:45]=[CH:44][C:43]([S:46]([CH3:49])(=[O:48])=[O:47])=[CH:42][CH:41]=3)=[CH:38][C:37]([CH2:50][C:51]([OH:53])=O)=[C:36]2[CH3:54])=[CH:31][CH:30]=1.[N+]([O-])([O-])=O.[NH2:59][C@@H:60]([CH2:64][O:65][N+:66]([O-:68])=[O:67])[C:61]([OH:63])=[O:62].Cl>C1COCC1>[O:65]([CH2:64][C@H:60]([NH:59][C:51](=[O:53])[CH2:50][C:37]1[CH:38]=[C:39]([C:40]2[CH:45]=[CH:44][C:43]([S:46]([CH3:49])(=[O:47])=[O:48])=[CH:42][CH:41]=2)[N:35]([C:32]2[CH:33]=[CH:34][C:29]([F:28])=[CH:30][CH:31]=2)[C:36]=1[CH3:54])[C:61]([OH:63])=[O:62])[N+:66]([O-:68])=[O:67]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 943NitrateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 56833630HCID 56833630, compoundHCID 86688740HCID 86688740, compound

Product 1

HCID 86688739HCID 86688739, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TEA (0.5 ml) and BOP (0.84 mmol) are added to a solution of acid 6g (0.7 mmol) in THF. After 1 h, the nitrate of (S)-2-amino-3-nitroxypropionic acid (1.5 mmol) is added and it is stirred for a further 2 h at RT. Then it is concentrated and the residue is dissolved in 10% K2CO3, then it is filtered. The solution thus obtained is acidified to pH 2 with 2N HCl and the precipitate obtained is filtered and dried; yield 80%, m.p. 109° C. FT-IR cm−1: 3300 (ν N—H), 1734 (ν C—O), 1640 (ν C—O), 1520 (δ N—H), 1278 (ν C—N), 1595 (νasO—NO2), 865 (νsO—NO2). 1H NMR (400 MHz, CDCl3): δ 7.70 (d, 2H), 7.30 (m, 4H), 7.23 (m, 2H), 6.73 (s broad, 1H), 6.50 (s, 1H), 4.70 (m, 1H), 4.20 (m, 2H), 3.54 (s, 2H), 3.01 (s, 3H), 2.07 (s, 3H).

Workup

  1. concentrationThen it is concentrated
  2. dissolutionthe residue is dissolved in 10% K2CO3
  3. filtrationit is filtered
  4. customThe solution thus obtained
  5. customthe precipitate obtained
  6. filtrationis filtered
  7. customdried

Sources & evidence

ORD record
ord-73933bbca458467ba2b00f4e987bbc9c
Source dataset
uspto-grants-2015_10
Patent number
US09162979B2

Reaction notes

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