Glycolaldehyde dimer → HCID 73055734, compound

HRID 1055467Notes

Reaction equation

HRID 1055467 reaction equation
[BH-](OC(C)=O)(OC(C)=O)[O:2][C:3]([CH3:5])=O.[Na+].[NH2:15][C@@H:16]([CH3:50])[C:17]([NH:19][C@H:20]1[CH2:26][O:25][C:24]2[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=2[N:22]([CH2:31][C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[C:47]#[N:48])[N:33]=2)[C:21]1=[O:49])=[O:18].C1OC(O)COC1O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:47]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[N:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:32]([CH2:31][N:22]2[C:21](=[O:49])[C@@H:20]([NH:19][C:17](=[O:18])[C@@H:16]([NH:15][CH2:5][CH2:3][OH:2])[CH3:50])[CH2:26][O:25][C:24]3[CH:27]=[CH:28][CH:29]=[CH:30][C:23]2=3)=[N:33]1)#[N:48]

Participants

6

Reactant 3

HCID 186078Glycolaldehyde dimerHCID 5049666Sodium triacetoxyborohydrideHCID 73055729HCID 73055729, compound

Product 1

HCID 73055734HCID 73055734, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Na(OAc)3BH (14.2 mg, 67.0 μmol, Eq: 1.4) was added to a solution of (S)-2-amino-N-((S)-5-((1-(2-cyanophenyl)-1H-indazol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)propanamide (23 mg, 47.9 μmol, Eq: 1.00) and glycolaldehyde dimer (3.16 mg, 26.3 μmol, Eq: 0.55) in DCM (1.5 mL). After 72 h. at RT, the mixture was diluted with NaHCO3 and extracted with DCMThecombined extracts were concentrated. The residue was purified by preparative TLC to give the title compound (16 mg, 95%) as a solid. MS m/z 525 (MH+)

Workup

  1. extractionextracted with DCMThecombined extracts
  2. concentrationwere concentrated
  3. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-374506892a10403fadaaec4491d9399a
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

Loading…